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Project uploaded by:	Rajib
Project ID:	IMP_100015
Title:	Metabolite profiling of MNBM by LC-MS/MS
Project Description:	Metabolite profiling of Mahonia napaulensis bark methanol extract (MNBM) of Nepal by LC-MS/MS
Research Area:	Biological Sciences
Funding Source:	ICGEB, New Delhi
Project Contributors:	ICGEB, New Delhi and UGC, Nepal

Study uploaded by:	Rajib
Study ID:	IMS_100012
Title:	LC-MS/MS analysis of chloroform fraction (MNSMC) of methanol extract of stem of M. napaulensis.
Summary:	Metabolite profiling of most active chloroform fraction (MNSMC) by LC-MS/MS analysis Since chloroform fraction of methanol extract of M. napaulensis stem was the most active fraction, its metabolite profiling was done by LC-MS/MS analysis. The LC-MS/MS analysis identified 153 metabolites. The most abundant five metabolites are cetrimonium (36.82 %), berberine (11.14 %), (15Z)-9,12,13-Trihydroxy-15-octadecenoic acid (7.31 %), protopine (6.13%) and (5R,6S)-5-Hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one (3.31 %). The literature study through PubChem and Chemical Entities of Biological Interest (ChEBI) reported that the metabolites berberine (11.14 %), protopine (6.13%), luteolin (1.07%), apigenin (0.64%), menadione (0.29%), tangeretin (0.21%), matairesinol (0.16%), dioscin (0.15%), nobiletin (0.14%), (E)-dacarbazine (0.12%), salirasib (0.11%), NECA (0.03%), MTIC (0.02%), mitoxantrone (0.01%), hydroxytyrosol (0.01%), and betulin (0.01%) have anticancer activity.
Publication:
Release Date:	Dec. 20, 2024
Study Type:	Mass Spectrometry (MS)
Data Type:	Untargeted
IEC/IBSC Approval Number :

Sr.No	Sample ID	Sample Name	Organism	Source	Sample Preparation Protocol	Sample Type	Experimental Condition	Time of treatment	Variant/Variety	Gender	Age	Replicates	Storage Conditions	Extraction Protocol
1	IMSM_100842	M. napaulensis Stem	Mahonia napaulensis	Mahonia napaulensis	The sample was dissolved in 200ul of 80% MeOH and mixed with a Vortexer. The samples were mixed for 5 min and centrifuged at 13,000 × g for 5 min to remove solid particles from the supernatant. 100ul supernatant was transferred into 150 μL glass insert in a 1.5 mL amber glass vial and analyzed by UHPLC-MS/MS.	Plant Sample (02)	Chloroform fraction (MNSMC) of methanol extract of stem of Mahonia napaulensis	NA	M. napaulensis	NA	NA	NA	4oC	The plant stem was cleaned and shade dried. The dried plant stem was ground into fine powder. The extraction was done by cold maceration process using methanol solvent in closed vessel for three days at room temperature. The extract was collected. This process was repeated three times consecutively. The extract was filtered using Whatman filter paper No. 1. The filtered extract was dried under reduced pressure at room temperature below 40oC using rotary evaporator (BIOBASE RE-2000B Rotary Evaporator, China) and then, by using freeze dryer or lyophilizer. Then, the extract was stored in closed vials at 4oC for further analysis.
2	IMSM_100841	M. napaulensis Stem	Mahonia napaulensis	Mahonia napaulensis	The sample was dissolved in 200ul of 80% MeOH and mixed with a Vortexer. The samples were mixed for 5 min and centrifuged at 13,000 × g for 5 min to remove solid particles from the supernatant. 100ul supernatant was transferred into 150 μL glass insert in a 1.5 mL amber glass vial and analyzed by UHPLC-MS/MS.	Plant Sample	Chloroform fraction (MNSMC) of methanol extract of stem of Mahonia napaulensis	NA	M. napaulensis	NA	NA	NA	4oC	The plant stem was cleaned and shade dried. The dried plant stem was ground into fine powder. The extraction was done by cold maceration process using methanol solvent in closed vessel for three days at room temperature. The extract was collected. This process was repeated three times consecutively. The extract was filtered using Whatman filter paper No. 1. The filtered extract was dried under reduced pressure at room temperature below 40oC using rotary evaporator (BIOBASE RE-2000B Rotary Evaporator, China) and then, by using freeze dryer or lyophilizer. Then, the extract was stored in closed vials at 4oC for further analysis.

Sr.No	MS Exp ID	Technique	Sample Name/ID	Mass Spectrometer Type	MS Instrument Name	MS Instrument type	MS Ionization Method	Ion Mode/Scan Polarity	Data Transformation (Software/s Used)
1	IME_100490	MS (Mass Spectrometry)	M. napaulensis Stem / IMSM_100841	LCMS (Liquid Chromatography- Mass Spectrometry)	Thermo Q Exactive Plus Orbitarp	Orbitrap	Others	Positive	Compound Discoverer
2	IME_100491	MS (Mass Spectrometry)	M. napaulensis Stem / IMSM_100842	LCMS (Liquid Chromatography- Mass Spectrometry)	Thermo Q Exactive Plus Orbitarp	Orbitrap	Others	Negative	Compound Discoverer

Sr.No	First name	Last name	Email	Organization	Designation
1	Rajib	Kumar Shrestha	shrestharajib2005@ku.edu.np	Kathmandu University, Nepal	scientist

Sr.No	ftprun ID	MS Exp ID	MS Data Files
1	IMR_101089	IME_100490	Mahonia_napaulensis_Stem_P.raw
2	IMR_101090	IME_100491	Mahonia_napaulensis_Stem_N.raw

Metabolite/Compound File: Chloform fraction_1.xlsx

Sr.No	Structure	Details
1		Cetrimonium CHEBI ID: CHEBI:39561 PubChem ID: 2681 Chemical Formula: C19 H41 N Smiles: CCCCCCCCCCCCCCCC[N+](C)(C)C InChI: InChI=1S/C19H42N/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4/h5-19H2,1-4H3/q+1 Mass to charge: 284.32941 Retention Time: 10.259
2		Berberine CHEBI ID: CHEBI:16118 PubChem ID: 2353 Chemical Formula: C20 H17 N O4 Smiles: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC InChI: InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1 Mass to charge: 336.12097 Retention Time: 6.579
3		(15Z)-9,12,13-Trihydroxy-15-octadecenoic acid CHEBI ID: CHEBI:139445 PubChem ID: 24066906 Chemical Formula: C18 H34 O5 Smiles: CCC=CCC(C(CCC(CCCCCCCC(=O)O)O)O)O InChI: InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,15-17,19-21H,2,4-6,8-14H2,1H3,(H,22,23)/b7-3- Mass to charge: 329.23108 Retention Time: 7.575
4		Protopine CHEBI ID: CHEBI:16415 PubChem ID: 4970 Chemical Formula: C20 H19 N O5 Smiles: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3 InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 Mass to charge: 354.1315 Retention Time: 7.496
5		(5R,6S)-5-Hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one CHEBI ID: CHEBI:181514 PubChem ID: 10944777 Chemical Formula: C14 H16 O4 Smiles: COC1=CC(=O)O[C@@H](CCc2ccccc2)[C@H]1O InChI: InChI=1S/C14H16O4/c1-17-12-9-13(15)18-11(14(12)16)8-7-10-5-3-2-4-6-10/h2-6,9,11,14,16H,7-8H2,1H3/t11-,14+/m0/s1 Mass to charge: 249.11073 Retention Time: 6.456
6		4-morpholinobenzoic acid CHEBI ID: CHEBI:183418 PubChem ID: 345278 Chemical Formula: C11 H13 N O3 Smiles: C1COCCN1C2=CC=C(C=C2)C(=O)O InChI: InChI=1S/C11H13NO3/c13-11(14)9-1-3-10(4-2-9)12-5-7-15-8-6-12/h1-4H,5-8H2,(H,13,14) Mass to charge: 208.0957 Retention Time: 5.667
7		Corchorifatty acid F CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H32 O5 Smiles: CC/C=C\CC(O)C(O)/C=C/C(O)CCCCCCCC(=O)O InChI: InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+ Mass to charge: 327.21536 Retention Time: 7.335
8		Caprolactam CHEBI ID: CHEBI:28579 PubChem ID: 7768 Chemical Formula: C6 H11 N O Smiles: C1CCC(=O)NCC1 InChI: InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8) Mass to charge: 114.09104 Retention Time: 2.266
9		1-phenyl-N-(6-quinoxalinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide CHEBI ID: NA PubChem ID: NA Chemical Formula: C19 H12 F3 N5 O Smiles: O=C(Nc1ccc2nccnc2c1)c1cnn(-c2ccccc2)c1C(F)(F)F InChI: InChI=1S/C19H12F3N5O/c20-19(21,22)17-14(11-25-27(17)13-4-2-1-3-5-13)18(28)26-12-6-7-15-16(10-12)24-9-8-23-15/h1-11H,(H,26,28) Mass to charge: 384.10559 Retention Time: 7.236
10		16-Hydroxyhexadecanoic acid CHEBI ID: CHEBI:55328 PubChem ID: 10466 Chemical Formula: C16 H32 O3 Smiles: C(CCCCCCCC(=O)O)CCCCCCCO InChI: InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19) Mass to charge: 271.22604 Retention Time: 11.395
11		Sorbic acid CHEBI ID: CHEBI:35962 PubChem ID: 643460 Chemical Formula: C6 H8 O2 Smiles: CC=CC=CC(=O)O InChI: InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+ Mass to charge: 113.05943 Retention Time: 2.219
12		9-Oxo-10(E),12(E)-octadecadienoic acid CHEBI ID: CHEBI:72843 PubChem ID: 5283011 Chemical Formula: C18 H30 O3 Smiles: CCCCCC=CC=CC(=O)CCCCCCCC(=O)O InChI: InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+ Mass to charge: 295.22482 Retention Time: 10.296
13		13(S)-HOTrE CHEBI ID: CHEBI:84441 PubChem ID: 16061072 Chemical Formula: C18 H30 O3 Smiles: CCC=CCC(C=CC=CCCCCCCCC(=O)O)O InChI: InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)/b9-7-,11-3-,15-12+/t17-/m0/s1 Mass to charge: 293.2103 Retention Time: 9.519
14		Ostruthin CHEBI ID: CHEBI:69833 PubChem ID: 5281420 Chemical Formula: C19 H22 O3 Smiles: CC(=CCCC(=CCC1=C(C=C2C(=C1)C=CC(=O)O2)O)C)C InChI: InChI=1S/C19H22O3/c1-13(2)5-4-6-14(3)7-8-15-11-16-9-10-19(21)22-18(16)12-17(15)20/h5,7,9-12,20H,4,6,8H2,1-3H3/b14-7+ Mass to charge: 297.15088 Retention Time: 10.075
15		Luteolin CHEBI ID: CHEBI:15864 PubChem ID: 5280445 Chemical Formula: C15 H10 O6 Smiles: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O InChI: InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H Mass to charge: 285.03854 Retention Time: 9.651
16		5-Hydroxyindole-3-acetic acid CHEBI ID: CHEBI:27823 PubChem ID: 1826 Chemical Formula: C10 H9 N O3 Smiles: C1=CC2=C(C=C1O)C(=CN2)CC(=O)O InChI: InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14) Mass to charge: 192.06447 Retention Time: 6.079
17		1-(4-Methylphenyl)pyrrolidine-2,5-dione CHEBI ID: CHEBI:170030 PubChem ID: 75335 Chemical Formula: C11 H11 N O2 Smiles: CC1=CC=C(C=C1)N2C(=O)CCC2=O InChI: InChI=1S/C11H11NO2/c1-8-2-4-9(5-3-8)12-10(13)6-7-11(12)14/h2-5H,6-7H2,1H3 Mass to charge: 190.08525 Retention Time: 1.83
18		Myristyl sulfate CHEBI ID: CHEBI:135234 PubChem ID: 5248 Chemical Formula: C14 H30 O4 S Smiles: CCCCCCCCCCCCCCOS(=O)(=O)O InChI: InChI=1S/C14H30O4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17/h2-14H2,1H3,(H,15,16,17) Mass to charge: 293.17722 Retention Time: 11.655
19		Apigenin CHEBI ID: CHEBI:18388 PubChem ID: 5280443 Chemical Formula: C15 H10 O5 Smiles: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H Mass to charge: 269.0437 Retention Time: 9.207
20		3-(1,1,2,3,3,3-hexafluoropropyl)adamantane-1-carboxylic acid CHEBI ID: CHEBI:183370 PubChem ID: 2729448 Chemical Formula: C14 H16 F6 O2 Smiles: C1C2CC3(CC1CC(C2)(C3)C(C(C(F)(F)F)F)(F)F)C(=O)O InChI: InChI=1S/C14H16F6O2/c15-9(14(18,19)20)13(16,17)12-4-7-1-8(5-12)3-11(2-7,6-12)10(21)22/h7-9H,1-6H2,(H,21,22) Mass to charge: 329.10086 Retention Time: 7.134
21		phenothiazine CHEBI ID: CHEBI:37931 PubChem ID: 7108 Chemical Formula: C12 H9 N S Smiles: C1=CC=C2C(=C1)NC3=CC=CC=C3S2 InChI: InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H Mass to charge: 198.03879 Retention Time: 6.899
22		(+/-)9-HpODE CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H32 O4 Smiles: CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)OO InChI: InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+ Mass to charge: 311.22079 Retention Time: 9.863
23		Phloionolic acid CHEBI ID: CHEBI:133325 PubChem ID: 5282938 Chemical Formula: C18 H36 O5 Smiles: C(CCCCO)CCCC(C(CCCCCCCC(=O)O)O)O InChI: InChI=1S/C18H36O5/c19-15-11-7-2-1-4-8-12-16(20)17(21)13-9-5-3-6-10-14-18(22)23/h16-17,19-21H,1-15H2,(H,22,23) Mass to charge: 445.24115 Retention Time: 7.842
24		1-{2-[(4-fluorophenyl)sulfonyl]ethyl}-4-(2-pyridinyl)piperazine CHEBI ID: NA PubChem ID: 2810612 Chemical Formula: C17 H20 F N3 O2 S Smiles: C1CN(CCN1CCS(=O)(=O)C2=CC=C(C=C2)F)C3=CC=CC=N3 InChI: InChI=1S/C17H20FN3O2S/c18-15-4-6-16(7-5-15)24(22,23)14-13-20-9-11-21(12-10-20)17-3-1-2-8-19-17/h1-8H,9-14H2 Mass to charge: 350.13672 Retention Time: 7.017
25		3-Pyridylacetic acid CHEBI ID: CHEBI:86390 PubChem ID: 108 Chemical Formula: C7 H7 N O2 Smiles: C1=CC(=CN=C1)CC(=O)O InChI: InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10) Mass to charge: 138.05431 Retention Time: 3.023
26		aspoquinolone A CHEBI ID: CHEBI:177743 PubChem ID: 16085089 Chemical Formula: C27 H31 N O6 Smiles: CC1(C2CC2C(O1)(C)C=CC3=C(C4=C(C=C3)NC(=O)C(C4(C5=CC=C(C=C5)OC)O)OC)O)C InChI: InChI=1S/C27H31NO6/c1-25(2)18-14-19(18)26(3,34-25)13-12-15-6-11-20-21(22(15)29)27(31,23(33-5)24(30)28-20)16-7-9-17(32-4)10-8-16/h6-13,18-19,23,29,31H,14H2,1-5H3,(H,28,30)/b13-12+/t18-,19+,23+,26-,27-/m1/s1 Mass to charge: 488.20422 Retention Time: 6.913
27		ethyl 3-[(1-benzyl-4-piperidyl)amino]-2-cyanoacrylate CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H23 N3 O2 Smiles: CCOC(=O)/C(C#N)=C/NC1CCN(Cc2ccccc2)CC1 InChI: InChI=1S/C18H23N3O2/c1-2-23-18(22)16(12-19)13-20-17-8-10-21(11-9-17)14-15-6-4-3-5-7-15/h3-7,13,17,20H,2,8-11,14H2,1H3/b16-13+ Mass to charge: 312.16989 Retention Time: 10.768
28		Linoleoyl Ethanolamide CHEBI ID: CHEBI:64032 PubChem ID: 5283446 Chemical Formula: C20 H37 N O2 Smiles: CCCCCC=CCC=CCCCCCCCC(=O)NCCO InChI: InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9- Mass to charge: 324.2876 Retention Time: 10.907
29		3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene CHEBI ID: CHEBI:91709 PubChem ID: 5417 Chemical Formula: C21 H25 N O4 Smiles: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC InChI: InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3 Mass to charge: 356.18332 Retention Time: 5.733
30		4-Pyridineacetic acid CHEBI ID: NA PubChem ID: 34228 Chemical Formula: C7 H7 N O2 Smiles: C1=CN=CC=C1CC(=O)O InChI: InChI=1S/C7H7NO2/c9-7(10)5-6-1-3-8-4-2-6/h1-4H,5H2,(H,9,10) Mass to charge: 138.05428 Retention Time: 2.689
31		Payzone CHEBI ID: CHEBI:229883 PubChem ID: 107975 Chemical Formula: C14 H12 N6 O6 Smiles: C1=C(OC(=C1)[N+](=O)[O-])C=CC(=NN=C(N)N)C=CC2=CC=C(O2)[N+](=O)[O-].Cl InChI: InChI=1S/C14H12N6O6.ClH/c15-14(16)18-17-9(1-3-10-5-7-12(25-10)19(21)22)2-4-11-6-8-13(26-11)20(23)24;/h1-8H,(H4,15,16,18);1H Mass to charge: 359.07486 Retention Time: 7.93
32		Dibutyl sebacate CHEBI ID: CHEBI:165632 PubChem ID: 7986 Chemical Formula: C18 H34 O4 Smiles: CCCCOC(=O)CCCCCCCCC(=O)OCCCC InChI: InChI=1S/C18H34O4/c1-3-5-15-21-17(19)13-11-9-7-8-10-12-14-18(20)22-16-6-4-2/h3-16H2,1-2H3 Mass to charge: 337.23282 Retention Time: 9.113
33		(3aR,7aS,8S,9aR)-5,8-dimethyl-3-methylidene-2H,3H,3aH,4H,6H,7H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione CHEBI ID: NA PubChem ID: NA Chemical Formula: C15 H18 O3 Smiles: NA InChI: NA Mass to charge: 247.13155 Retention Time: 9.431
34		Menadione CHEBI ID: CHEBI:28869 PubChem ID: 4055 Chemical Formula: C11 H8 O2 Smiles: CC1=CC(=O)C2=CC=CC=C2C1=O InChI: InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Mass to charge: 205.0849 Retention Time: 6.916
35		Dibutyl phthalate CHEBI ID: CHEBI:34687 PubChem ID: 3026 Chemical Formula: C16 H22 O4 Smiles: CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC InChI: InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 Mass to charge: 279.1575 Retention Time: 10.396
36		4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole CHEBI ID: CHEBI:68234 PubChem ID: 4276 Chemical Formula: C11 H12 O3 Smiles: COC1=CC(=CC2=C1OCO2)CC=C InChI: InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3 Mass to charge: 193.08496 Retention Time: 6.854
37		Carbofuran CHEBI ID: CHEBI:34611 PubChem ID: 2566 Chemical Formula: C12 H15 N O3 Smiles: CC1(CC2=C(O1)C(=CC=C2)OC(=O)NC)C InChI: InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14) Mass to charge: 222.1113 Retention Time: 6.324
38		[1,1'-biphenyl]-2,2'-dicarboxylic acid CHEBI ID: CHEBI:23837 PubChem ID: 10210 Chemical Formula: C14 H10 O4 Smiles: C1=CC=C(C(=C1)C2=CC=CC=C2C(=O)O)C(=O)O InChI: InChI=1S/C14H10O4/c15-13(16)11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(17)18/h1-8H,(H,15,16)(H,17,18) Mass to charge: 241.04868 Retention Time: 7.362
39		3-tert-Butyladipic acid CHEBI ID: CHEBI:167756 PubChem ID: 98967 Chemical Formula: C10 H18 O4 Smiles: CC(C)(C)C(CCC(=O)O)CC(=O)O InChI: InChI=1S/C10H18O4/c1-10(2,3)7(6-9(13)14)4-5-8(11)12/h7H,4-6H2,1-3H3,(H,11,12)(H,13,14) Mass to charge: 201.11122 Retention Time: 6.933
40		(2E)-3-(4-Acetoxy-2,3-dihydroxy-2,5,5,8a-tetramethyldecahydro-1-naphthalenyl)acrylic acid CHEBI ID: NA PubChem ID: NA Chemical Formula: C19 H30 O6 Smiles: CC(=O)OC1C(O)C(C)(O)C(/C=C/C(=O)O)C2(C)CCCC(C)(C)C12 InChI: InChI=1S/C19H30O6/c1-11(20)25-14-15-17(2,3)9-6-10-18(15,4)12(7-8-13(21)22)19(5,24)16(14)23/h7-8,12,14-16,23-24H,6,9-10H2,1-5H3,(H,21,22)/b8-7+ Mass to charge: 353.19791 Retention Time: 11.131
41		1,4-Bis(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan CHEBI ID: NA PubChem ID: NA Chemical Formula: C24 H30 O8 Smiles: NA InChI: NA Mass to charge: 447.19897 Retention Time: 8.395
42		(+/-)12(13)-DiHOME CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H34 O4 Smiles: CCCCC[C@@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O InChI: InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17+/m1/s1 Mass to charge: 337.23294 Retention Time: 9.014
43		Tridemorph CHEBI ID: CHEBI:83365 PubChem ID: 32518 Chemical Formula: C19 H39 N O Smiles: CCCCCCCCCCCCCN1CC(OC(C1)C)C InChI: InChI=1S/C19H39NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-20-16-18(2)21-19(3)17-20/h18-19H,4-17H2,1-3H3 Mass to charge: 298.30869 Retention Time: 9.183
44		1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one CHEBI ID: CHEBI:228382 PubChem ID: 442916 Chemical Formula: C13 H16 O2 Smiles: CC(=CCC1=C(C=CC(=C1)C(=O)C)O)C InChI: InChI=1S/C13H16O2/c1-9(2)4-5-12-8-11(10(3)14)6-7-13(12)15/h4,6-8,15H,5H2,1-3H3 Mass to charge: 205.12125 Retention Time: 7.037
45		Tangeritin CHEBI ID: CHEBI:9400 PubChem ID: 68077 Chemical Formula: C20 H20 O7 Smiles: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC InChI: InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3 Mass to charge: 373.12604 Retention Time: 8.75
46		ethyl 4-{[4-(tert-butyl)anilino]sulfonyl}-5-(4-chlorophenyl)-2-methyl-3-furoate CHEBI ID: NA PubChem ID: NA Chemical Formula: C24 H26 Cl N O5 S Smiles: CCOC(=O)c1c(C)oc(-c2ccc(Cl)cc2)c1S(=O)(=O)Nc1ccc(C(C)(C)C)cc1 InChI: InChI=1S/C24H26ClNO5S/c1-6-30-23(27)20-15(2)31-21(16-7-11-18(25)12-8-16)22(20)32(28,29)26-19-13-9-17(10-14-19)24(3,4)5/h7-14,26H,6H2,1-5H3 Mass to charge: 476.13153 Retention Time: 8.379
47		(2S)-2-Amino-4-hexynoic acid CHEBI ID: NA PubChem ID: 10654237 Chemical Formula: C6 H9 N O2 Smiles: CC#CCC(C(=O)O)N InChI: InChI=1S/C6H9NO2/c1-2-3-4-5(7)6(8)9/h5H,4,7H2,1H3,(H,8,9)/t5-/m0/s1 Mass to charge: 111.04375 Retention Time: 1.327
48		N-tert-Butyloxycarbonyl-deacetyl-leupeptin CHEBI ID: CHEBI:7352 PubChem ID: 443303 Chemical Formula: C23 H44 N6 O5 Smiles: CC(C)CC(C(=O)NC(CCCN=C(N)N)C=O)NC(=O)C(CC(C)C)NC(=O)OC(C)(C)C InChI: InChI=1S/C23H44N6O5/c1-14(2)11-17(19(31)27-16(13-30)9-8-10-26-21(24)25)28-20(32)18(12-15(3)4)29-22(33)34-23(5,6)7/h13-18H,8-12H2,1-7H3,(H,27,31)(H,28,32)(H,29,33)(H4,24,25,26)/t16?,17?,18-/m0/s1 Mass to charge: 502.37088 Retention Time: 10.71
49		AM-Toxin I CHEBI ID: CHEBI:80726 PubChem ID: 3035206 Chemical Formula: C23 H31 N3 O6 Smiles: CC1C(=O)OC(C(=O)NC(C(=O)NC(=C)C(=O)N1)CCCC2=CC=C(C=C2)OC)C(C)C InChI: InChI=1S/C23H31N3O6/c1-13(2)19-22(29)26-18(8-6-7-16-9-11-17(31-5)12-10-16)21(28)24-14(3)20(27)25-15(4)23(30)32-19/h9-13,15,18-19H,3,6-8H2,1-2,4-5H3,(H,24,28)(H,25,27)(H,26,29)/t15-,18-,19-/m0/s1 Mass to charge: 478.25616 Retention Time: 8.274
50		2-[(3S)-1-(4-Chlorobenzyl)-3-pyrrolidinyl]-5-(trifluoromethyl)-1H-benzimidazole CHEBI ID: NA PubChem ID: NA Chemical Formula: C19 H17 Cl F3 N3 Smiles: FC(F)(F)c1ccc2nc([C@H]3CCN(Cc4ccc(Cl)cc4)C3)[nH]c2c1 InChI: InChI=1S/C19H17ClF3N3/c20-15-4-1-12(2-5-15)10-26-8-7-13(11-26)18-24-16-6-3-14(19(21,22)23)9-17(16)25-18/h1-6,9,13H,7-8,10-11H2,(H,24,25)/t13-/m0/s1 Mass to charge: 380.11078 Retention Time: 7.115
51		3-Phenylpropanoic acid CHEBI ID: CHEBI:28631 PubChem ID: 107 Chemical Formula: C9 H10 O2 Smiles: C1=CC=C(C=C1)CCC(=O)O InChI: InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) Mass to charge: 364.15216 Retention Time: 7.334
52		N1-(1-Phenylethyl)-3,4,5-trimethoxybenzamide CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H21 N O4 Smiles: COc1cc(C(=O)NC(C)c2ccccc2)cc(OC)c1OC InChI: InChI=1S/C18H21NO4/c1-12(13-8-6-5-7-9-13)19-18(20)14-10-15(21-2)17(23-4)16(11-14)22-3/h5-12H,1-4H3,(H,19,20) Mass to charge: 316.1524 Retention Time: 8.085
53		Matairesinol CHEBI ID: CHEBI:6698 PubChem ID: 119205 Chemical Formula: C20 H22 O6 Smiles: COC1=C(C=CC(=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)O InChI: InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1 Mass to charge: 403.13705 Retention Time: 7.377
54		Dioscin CHEBI ID: CHEBI:74023 PubChem ID: 119245 Chemical Formula: C45 H72 O16 Smiles: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1 InChI: InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1 Mass to charge: 433.23297 Retention Time: 11.641
55		L-Tyrosine CHEBI ID: CHEBI:17895 PubChem ID: 6057 Chemical Formula: C9 H11 N O3 Smiles: C1=CC(=CC=C1CC(C(=O)O)N)O InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 Mass to charge: 182.08017 Retention Time: 5.299
56		3,8,9-trihydroxy-10-propyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one CHEBI ID: CHEBI:183349 PubChem ID: 75110872 Chemical Formula: C12 H20 O5 Smiles: CCCC1C(C(C=CCCC(C(=O)O1)O)O)O InChI: InChI=1S/C12H20O5/c1-2-5-10-11(15)8(13)6-3-4-7-9(14)12(16)17-10/h3,6,8-11,13-15H,2,4-5,7H2,1H3 Mass to charge: 243.12192 Retention Time: 6.679
57		6-Acetylcodeine CHEBI ID: NA PubChem ID: 5486550 Chemical Formula: C20 H23 N O4 Smiles: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C InChI: InChI=1S/C20H23NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4-7,13-14,16,19H,8-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1 Mass to charge: 342.16803 Retention Time: 5.162
58		1-{3-[3,5-di(trifluoromethyl)phenyl]prop-2-ynyl}piperidine hydrochloride CHEBI ID: NA PubChem ID: NA Chemical Formula: C16 H15 F6 N Smiles: Cl.FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 InChI: InChI=1S/C16H15F6N.ClH/c17-15(18,19)13-9-12(10-14(11-13)16(20,21)22)5-4-8-23-6-2-1-3-7-23;/h9-11H,1-3,6-8H2;1H Mass to charge: 336.12091 Retention Time: 10.694
59		2,3-Dinor-8-epi-prostaglandin F2α CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H30 O5 Smiles: CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CC(=O)O)[C@@H](O)C[C@H]1O InChI: InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13-,14-,15+,16-,17+/m0/s1 Mass to charge: 309.20435 Retention Time: 7.654
60		alanycarb CHEBI ID: CHEBI:38463 PubChem ID: 9576091 Chemical Formula: C17 H25 N3 O4 S2 Smiles: CCOC(=O)CCN(CC1=CC=CC=C1)SN(C)C(=O)ON=C(C)SC InChI: InChI=1S/C17H25N3O4S2/c1-5-23-16(21)11-12-20(13-15-9-7-6-8-10-15)26-19(3)17(22)24-18-14(2)25-4/h6-10H,5,11-13H2,1-4H3/b18-14- Mass to charge: 400.13675 Retention Time: 7.871
61		Nobiletin CHEBI ID: CHEBI:7602 PubChem ID: 72344 Chemical Formula: C21 H22 O8 Smiles: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC InChI: InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3 Mass to charge: 403.13651 Retention Time: 8.335
62		Oleamide CHEBI ID: CHEBI:116314 PubChem ID: 5283387 Chemical Formula: C18 H35 N O Smiles: CCCCCCCCC=CCCCCCCCC(=O)N InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9- Mass to charge: 282.2775 Retention Time: 12.01
63		N-Benzyl-N-methyl-2-[(3R,4S)-3-({5-[(phenylsulfanyl)methyl]-1,2-oxazol-3-yl}methyl)-4-piperidinyl]acetamide CHEBI ID: NA PubChem ID: NA Chemical Formula: C26 H31 N3 O2 S Smiles: CN(Cc1ccccc1)C(=O)C[C@@H]1CCNC[C@@H]1Cc1cc(CSc2ccccc2)on1 InChI: InChI=1S/C26H31N3O2S/c1-29(18-20-8-4-2-5-9-20)26(30)15-21-12-13-27-17-22(21)14-23-16-24(31-28-23)19-32-25-10-6-3-7-11-25/h2-11,16,21-22,27H,12-15,17-19H2,1H3/t21-,22-/m0/s1 Mass to charge: 450.22501 Retention Time: 7.078
64		N-(2-{4-[5-(Acetylamino)-1H-benzimidazol-2-yl]phenyl}-1H-benzimidazol-5-yl)acetamide CHEBI ID: NA PubChem ID: NA Chemical Formula: C24 H20 N6 O2 Smiles: CC(=O)Nc1ccc2[nH]c(-c3ccc(-c4nc5cc(NC(C)=O)ccc5[nH]4)cc3)nc2c1 InChI: InChI=1S/C24H20N6O2/c1-13(31)25-17-7-9-19-21(11-17)29-23(27-19)15-3-5-16(6-4-15)24-28-20-10-8-18(26-14(2)32)12-22(20)30-24/h3-12H,1-2H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30) Mass to charge: 425.16824 Retention Time: 7.032
65		5-[4-(3-hydroxy-4-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol CHEBI ID: NA PubChem ID: NA Chemical Formula: C20 H22 O6 Smiles: NA InChI: NA Mass to charge: 359.14667 Retention Time: 6.72
66		Asarone CHEBI ID: CHEBI:78309 PubChem ID: 636822 Chemical Formula: C12 H16 O3 Smiles: CC=CC1=CC(=C(C=C1OC)OC)OC InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ Mass to charge: 480.23532 Retention Time: 7.427
67		8-{3-Oxo-2-[(2E)-2-penten-1-yl]-1-cyclopenten-1-yl}octanoic acid CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H28 O3 Smiles: CC/C=C/CC1=C(CCCCCCCC(=O)O)CCC1=O InChI: InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7H,2,4-6,8-14H2,1H3,(H,20,21)/b7-3+ Mass to charge: 293.20938 Retention Time: 9.565
68		(E)-Dacarbazine CHEBI ID: CHEBI:177836 PubChem ID: 135398738 Chemical Formula: C6 H10 N6 O Smiles: CN(C)N=NC1=C(NC=N1)C(=O)N InChI: InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+ Mass to charge: 181.0849 Retention Time: 7.359
69		Ectocarpene CHEBI ID: CHEBI:80847 PubChem ID: 12491370 Chemical Formula: C11 H16 Smiles: CCC=CC1CC=CCC=C1 InChI: InChI=1S/C11H16/c1-2-3-8-11-9-6-4-5-7-10-11/h3-4,6-8,10-11H,2,5,9H2,1H3/b8-3-/t11-/m0/s1 Mass to charge: 149.13176 Retention Time: 7.574
70		salirasib CHEBI ID: CHEBI:177460 PubChem ID: 5469318 Chemical Formula: C22 H30 O2 S Smiles: CC(=CCCC(=CCCC(=CCSC1=CC=CC=C1C(=O)O)C)C)C InChI: InChI=1S/C22H30O2S/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-25-21-14-6-5-13-20(21)22(23)24/h5-6,9,11,13-15H,7-8,10,12,16H2,1-4H3,(H,23,24)/b18-11+,19-15+ Mass to charge: 357.18954 Retention Time: 9.814
71		Cuminaldehyde CHEBI ID: CHEBI:28671 PubChem ID: 326 Chemical Formula: C10 H12 O Smiles: CC(C)C1=CC=C(C=C1)C=O InChI: InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 Mass to charge: 149.09537 Retention Time: 6.853
72		Pirolate CHEBI ID: NA PubChem ID: 135445830 Chemical Formula: C16 H15 N3 O5 Smiles: CCOC(=O)C1=NC2=C(C=C3C=C(C(=CC3=N2)OC)OC)C(=O)N1 InChI: InChI=1S/C16H15N3O5/c1-4-24-16(21)14-18-13-9(15(20)19-14)5-8-6-11(22-2)12(23-3)7-10(8)17-13/h5-7H,4H2,1-3H3,(H,17,18,19,20) Mass to charge: 330.10785 Retention Time: 6.917
73		(2'R,3R,4'R,4a'R,5S,8a'S)-5-(3-Furyl)-4'-hydroxy-4a',5'-bis(hydroxymethyl)-2'-methyl-3',4,4',4a',5,7',8',8a'-octahydro-2'H-spiro[furan-3,1'-naphthalen]-2-one CHEBI ID: NA PubChem ID: NA Chemical Formula: C20 H26 O6 Smiles: C[C@@H]1C[C@@H](O)[C@@]2(CO)C(CO)=CCC[C@@H]2[C@@]12C[C@@H](c1ccoc1)OC2=O InChI: InChI=1S/C20H26O6/c1-12-7-17(23)20(11-22)14(9-21)3-2-4-16(20)19(12)8-15(26-18(19)24)13-5-6-25-10-13/h3,5-6,10,12,15-17,21-23H,2,4,7-9,11H2,1H3/t12-,15+,16-,17-,19-,20+/m1/s1 Mass to charge: 407.16827 Retention Time: 6.431
74		4-(2,3-dihydro-1,4-benzodioxin-6-yl)butanoic acid CHEBI ID: CHEBI:183779 PubChem ID: 2775720 Chemical Formula: C12 H14 O4 Smiles: C1COC2=C(O1)C=CC(=C2)CCCC(=O)O InChI: InChI=1S/C12H14O4/c13-12(14)3-1-2-9-4-5-10-11(8-9)16-7-6-15-10/h4-5,8H,1-3,6-7H2,(H,13,14) Mass to charge: 223.09526 Retention Time: 7.046
75		Thiothixene CHEBI ID: CHEBI:9571 PubChem ID: 941651 Chemical Formula: C23 H29 N3 O2 S2 Smiles: CN1CCN(CC1)CCC=C2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)N(C)C InChI: InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8- Mass to charge: 444.17801 Retention Time: 7.172
76		Maltol CHEBI ID: CHEBI:69438 PubChem ID: 8369 Chemical Formula: C6 H6 O3 Smiles: CC1=C(C(=O)C=CO1)O InChI: InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3 Mass to charge: 127.03842 Retention Time: 1.138
77		α-Pyrrolidinobutiophenone CHEBI ID: NA PubChem ID: NA Chemical Formula: C14 H19 N O Smiles: CCC(C(=O)c1ccccc1)N1CCCC1 InChI: InChI=1S/C14H19NO/c1-2-13(15-10-6-7-11-15)14(16)12-8-4-3-5-9-12/h3-5,8-9,13H,2,6-7,10-11H2,1H3 Mass to charge: 218.15279 Retention Time: 4.839
78		4'-Methoxyacetophenone CHEBI ID: CHEBI:86567 PubChem ID: 7476 Chemical Formula: C9 H10 O2 Smiles: CC(=O)C1=CC=C(C=C1)OC InChI: InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3 Mass to charge: 151.07462 Retention Time: 6.271
79		2,2'-[(1R,3S,4R,6S)-2,4,5,6-Tetrahydroxy-1,3-cyclohexanediyl]diguanidine CHEBI ID: NA PubChem ID: NA Chemical Formula: C8 H18 N6 O4 Smiles: NC(N)=N[C@@H]1C(O)[C@H](N=C(N)N)[C@@H](O)C(O)[C@H]1O InChI: InChI=1S/C8H18N6O4/c9-7(10)13-1-3(15)2(14-8(11)12)5(17)6(18)4(1)16/h1-6,15-18H,(H4,9,10,13)(H4,11,12,14)/t1-,2+,3?,4+,5-,6? Mass to charge: 261.13254 Retention Time: 6.161
80		Dehydrovomifoliol CHEBI ID: CHEBI:4372 PubChem ID: 688492 Chemical Formula: C13 H18 O3 Smiles: CC1=CC(=O)CC(C1(C=CC(=O)C)O)(C)C InChI: InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1 Mass to charge: 508.26657 Retention Time: 7.924
81		1-[6,7-bis(2-methoxyethoxy)quinazolin-4-yl]piperidine-4-carboxylic acid CHEBI ID: NA PubChem ID: 2809621 Chemical Formula: C20 H27 N3 O6 Smiles: COCCOC1=C(C=C2C(=C1)C(=NC=N2)N3CCC(CC3)C(=O)O)OCCOC InChI: InChI=1S/C20H27N3O6/c1-26-7-9-28-17-11-15-16(12-18(17)29-10-8-27-2)21-13-22-19(15)23-5-3-14(4-6-23)20(24)25/h11-14H,3-10H2,1-2H3,(H,24,25) Mass to charge: 406.19897 Retention Time: 8.442
82		Erucamide CHEBI ID: CHEBI:142245 PubChem ID: 5365371 Chemical Formula: C22 H43 N O Smiles: CCCCCCCCC=CCCCCCCCCCCCC(=O)N InChI: InChI=1S/C22H43NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H2,23,24)/b10-9- Mass to charge: 338.33963 Retention Time: 14.262
83		(±)12(13)-DiHOME CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H34 O4 Smiles: CCCCC[C@@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O InChI: InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17+/m1/s1 Mass to charge: 313.23639 Retention Time: 10.312
84		Gusperimus CHEBI ID: CHEBI:135609 PubChem ID: 55362 Chemical Formula: C17 H37 N7 O3 Smiles: C(CCCN=C(N)N)CCC(=O)NC(C(=O)NCCCCNCCCN)O InChI: InChI=1S/C17H37N7O3/c18-9-7-11-21-10-5-6-12-22-15(26)16(27)24-14(25)8-3-1-2-4-13-23-17(19)20/h16,21,27H,1-13,18H2,(H,22,26)(H,24,25)(H4,19,20,23) Mass to charge: 370.29306 Retention Time: 10.765
85		3',5,7-Trihydroxy-4'-methoxyflavanone CHEBI ID: CHEBI:28230 PubChem ID: 72281 Chemical Formula: C16 H14 O6 Smiles: COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O InChI: InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Mass to charge: 301.06964 Retention Time: 7.031
86		1-(1,8-dihydroxy-3,6-dimethyl-2-naphthyl)ethan-1-one CHEBI ID: CHEBI:228709 PubChem ID: 283942 Chemical Formula: C14 H14 O3 Smiles: CC1=CC2=C(C(=C1)O)C(=C(C(=C2)C)C(=O)C)O InChI: InChI=1S/C14H14O3/c1-7-4-10-6-8(2)12(9(3)15)14(17)13(10)11(16)5-7/h4-6,16-17H,1-3H3 Mass to charge: 275.09067 Retention Time: 8.182
87		5-Amino-5-carboxy-2-hydroxy-1-pentene-1-diazonium CHEBI ID: NA PubChem ID: NA Chemical Formula: C6 H10 N3 O3 Smiles: N#[N+]C=C(O)CCC(N)C(=O)O InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H-,10,11,12)/p+1 Mass to charge: 173.07988 Retention Time: 1.11
88		9S,13R-12-Oxophytodienoic acid CHEBI ID: CHEBI:181862 PubChem ID: 14037063 Chemical Formula: C18 H28 O3 Smiles: CCC=CCC1C(C=CC1=O)CCCCCCCC(=O)O InChI: InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16+/m0/s1 Mass to charge: 293.20932 Retention Time: 9.973
89		L-lupinic acid CHEBI ID: CHEBI:6572 PubChem ID: 5280444 Chemical Formula: C13 H18 N6 O3 Smiles: CC(=CCNC1=C2C(=NC=N1)N(C=N2)CC(C(=O)O)N)CO InChI: InChI=1S/C13H18N6O3/c1-8(5-20)2-3-15-11-10-12(17-6-16-11)19(7-18-10)4-9(14)13(21)22/h2,6-7,9,20H,3-5,14H2,1H3,(H,21,22)(H,15,16,17)/b8-2+/t9-/m0/s1 Mass to charge: 305.13742 Retention Time: 8.721
90		N-Methyldioctylamine CHEBI ID: CHEBI:176815 PubChem ID: 78202 Chemical Formula: C17 H37 N Smiles: CCCCCCCCN(C)CCCCCCCC InChI: InChI=1S/C17H37N/c1-4-6-8-10-12-14-16-18(3)17-15-13-11-9-7-5-2/h4-17H2,1-3H3 Mass to charge: 256.29837 Retention Time: 9.559
91		canthin-6-one CHEBI ID: CHEBI:3363 PubChem ID: 97176 Chemical Formula: C14 H8 N2 O Smiles: C1=CC=C2C(=C1)C3=C4N2C(=O)C=CC4=NC=C3 InChI: InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H Mass to charge: 111.03889 Retention Time: 0.777
92		(9aR,9bS)-9a-Hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione CHEBI ID: NA PubChem ID: NA Chemical Formula: C15 H16 O4 Smiles: C=C1C(=O)O[C@H]2C1CCC(C)=C1C(=O)C=C(C)[C@@]12O InChI: InChI=1S/C15H16O4/c1-7-4-5-10-9(3)14(17)19-13(10)15(18)8(2)6-11(16)12(7)15/h6,10,13,18H,3-5H2,1-2H3/t10?,13-,15+/m0/s1 Mass to charge: 261.11066 Retention Time: 8.097
93		N-Acetyl-L-phenylalanine CHEBI ID: CHEBI:16259 PubChem ID: 74839 Chemical Formula: C11 H13 N O3 Smiles: CC(=O)NC(CC1=CC=CC=C1)C(=O)O InChI: InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1 Mass to charge: 206.08022 Retention Time: 5.695
94		glutathionylspermidine CHEBI ID: CHEBI:16613 PubChem ID: 440772 Chemical Formula: C17 H34 N6 O5 S Smiles: C(CCNCCCNC(=O)CNC(=O)C(CS)NC(=O)CCC(C(=O)O)N)CN InChI: InChI=1S/C17H34N6O5S/c18-6-1-2-7-20-8-3-9-21-15(25)10-22-16(26)13(11-29)23-14(24)5-4-12(19)17(27)28/h12-13,20,29H,1-11,18-19H2,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t12-,13-/m0/s1 Mass to charge: 433.22363 Retention Time: 8.153
95		6-Phenoxynicotinic acid CHEBI ID: CHEBI:167789 PubChem ID: 2776497 Chemical Formula: C12 H9 N O3 Smiles: C1=CC=C(C=C1)OC2=NC=C(C=C2)C(=O)O InChI: InChI=1S/C12H9NO3/c14-12(15)9-6-7-11(13-8-9)16-10-4-2-1-3-5-10/h1-8H,(H,14,15) Mass to charge: 248.09039 Retention Time: 4.76
96		Amide C18 CHEBI ID: CHEBI:34900 PubChem ID: 31292 Chemical Formula: C18 H37 N O Smiles: CCCCCCCCCCCCCCCCCC(=O)N InChI: InChI=1S/C18H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H2,19,20) Mass to charge: 284.29346 Retention Time: 12.972
97		Dodecanedioic acid CHEBI ID: CHEBI:4676 PubChem ID: 12736 Chemical Formula: C12 H22 O4 Smiles: C(CCCCCC(=O)O)CCCCC(=O)O InChI: InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) Mass to charge: 229.1425 Retention Time: 7.842
98		(2α,3β,19α)-2,3,19-Trihydroxyolean-12-en-28-oic acid CHEBI ID: NA PubChem ID: NA Chemical Formula: C30 H48 O5 Smiles: CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2[C@@H]1O InChI: InChI=1S/C30H48O5/c1-25(2)12-14-30(24(34)35)15-13-28(6)17(21(30)23(25)33)8-9-20-27(5)16-18(31)22(32)26(3,4)19(27)10-11-29(20,28)7/h8,18-23,31-33H,9-16H2,1-7H3,(H,34,35)/t18-,19+,20-,21-,22+,23+,27+,28-,29-,30+/m1/s1 Mass to charge: 533.34467 Retention Time: 8.695
99		1,2-dihydroxyheptadec-16-yn-4-yl acetate CHEBI ID: CHEBI:171809 PubChem ID: 45782986 Chemical Formula: C19 H34 O4 Smiles: CC(=O)OC(CCCCCCCCCCCC#C)CC(CO)O InChI: InChI=1S/C19H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-19(23-17(2)21)15-18(22)16-20/h1,18-20,22H,4-16H2,2H3 Mass to charge: 309.24045 Retention Time: 8.522
100		Triphenylphosphine oxide CHEBI ID: CHEBI:36601 PubChem ID: 13097 Chemical Formula: C18 H15 O P Smiles: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3 InChI: InChI=1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Mass to charge: 279.09177 Retention Time: 8.18
101		(+/-)13-HODE CHEBI ID: NA PubChem ID: NA Chemical Formula: C18 H32 O3 Smiles: CCCCCC(O)/C=C/C=C\CCCCCCCC(=O)O InChI: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+ Mass to charge: 295.22586 Retention Time: 10.591
102		Palmitoyl ethanolamide CHEBI ID: CHEBI:71464 PubChem ID: 4671 Chemical Formula: C18 H37 N O2 Smiles: CCCCCCCCCCCCCCCC(=O)NCCO InChI: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21) Mass to charge: 300.28784 Retention Time: 11.407
103		Decahydro-2-naphthalenecarboxylic acid CHEBI ID: CHEBI:34667 PubChem ID: 656885 Chemical Formula: C11 H18 O2 Smiles: C1CCC2CC(CCC2C1)C(=O)O InChI: InChI=1S/C11H18O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h8-10H,1-7H2,(H,12,13) Mass to charge: 183.13707 Retention Time: 6.428
104		4-(isopropylsulfonyl)-3-(methylthio)-1H-pyrazol-5-amine CHEBI ID: NA PubChem ID: NA Chemical Formula: C7 H13 N3 O2 S2 Smiles: CSc1n[nH]c(N)c1S(=O)(=O)C(C)C InChI: InChI=1S/C7H13N3O2S2/c1-4(2)14(11,12)5-6(8)9-10-7(5)13-3/h4H,1-3H3,(H3,8,9,10) Mass to charge: 234.03885 Retention Time: 6.034
105		2-Deoxystreptidine CHEBI ID: CHEBI:28248 PubChem ID: 439769 Chemical Formula: C8 H18 N6 O3 Smiles: C1C(C(C(C(C1N=C(N)N)O)O)O)N=C(N)N InChI: InChI=1S/C8H18N6O3/c9-7(10)13-2-1-3(14-8(11)12)5(16)6(17)4(2)15/h2-6,15-17H,1H2,(H4,9,10,13)(H4,11,12,14)/t2-,3+,4+,5-,6? Mass to charge: 245.13763 Retention Time: 6.924
106		Sudan III CHEBI ID: CHEBI:82535 PubChem ID: 62331 Chemical Formula: C22 H16 N4 O Smiles: C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N=NC3=C(C=CC4=CC=CC=C43)O InChI: InChI=1S/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H Mass to charge: 353.14319 Retention Time: 7.861
107		Oleoyl ethanolamide CHEBI ID: CHEBI:71466 PubChem ID: 5283454 Chemical Formula: C20 H39 N O2 Smiles: CCCCCCCCC=CCCCCCCCC(=O)NCCO InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9- Mass to charge: 326.30331 Retention Time: 11.558
108		2-({4-(1,3-benzodioxol-5-yl)-5-[4-(tert-butyl)phenyl]-4H-1,2,4-triazol-3-yl}sulfanyl)-1-phenyl-1-ethanone CHEBI ID: NA PubChem ID: NA Chemical Formula: C27 H25 N3 O3 S Smiles: CC(C)(C)c1ccc(-c2nnc(SCC(=O)c3ccccc3)n2-c2ccc3c(c2)OCO3)cc1 InChI: InChI=1S/C27H25N3O3S/c1-27(2,3)20-11-9-19(10-12-20)25-28-29-26(34-16-22(31)18-7-5-4-6-8-18)30(25)21-13-14-23-24(15-21)33-17-32-23/h4-15H,16-17H2,1-3H3 Mass to charge: 472.17264 Retention Time: 10.945
109		(1aR,2E,4aR,6S,7S,7aR,8R,11aS)-1,1,3,6-Tetramethyl-9-methylene-4-oxo-1,1a,4,5,6,7,7a,8,9,10,11,11a-dodecahydro-4aH-cyclopenta[a]cyclopropa[f][11]annulene-4a,7,8-triyl triacetate CHEBI ID: NA PubChem ID: NA Chemical Formula: C26 H36 O7 Smiles: C=C1CC[C@H]2[C@@H](/C=C(\C)C(=O)[C@@]3(OC(C)=O)C[C@H](C)[C@H](OC(C)=O)[C@@H]3[C@H]1OC(C)=O)C2(C)C InChI: InChI=1S/C26H36O7/c1-13-9-10-19-20(25(19,7)8)11-14(2)24(30)26(33-18(6)29)12-15(3)23(32-17(5)28)21(26)22(13)31-16(4)27/h11,15,19-23H,1,9-10,12H2,2-8H3/b14-11+/t15-,19-,20+,21-,22-,23-,26+/m0/s1 Mass to charge: 461.25089 Retention Time: 8.888
110		Linoleic Acid CHEBI ID: CHEBI:17351 PubChem ID: 5280450 Chemical Formula: C18 H32 O2 Smiles: CCCCCC=CCC=CCCCCCCCC(=O)O InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- Mass to charge: 279.23099 Retention Time: 11.8
111		Bis(2-ethylhexyl) phthalate CHEBI ID: CHEBI:17747 PubChem ID: 8343 Chemical Formula: C24 H38 O4 Smiles: CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC InChI: InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3 Mass to charge: 391.28201 Retention Time: 13.142
112		4,8-Dimethoxy-6,6-dimethyl-6,6a,12,12a,13a,14-hexahydro-5aH,13H-chromeno[3,2-b]xanthen-13-one CHEBI ID: NA PubChem ID: NA Chemical Formula: C24 H26 O5 Smiles: COc1cccc2c1OC1C(C2)C(=O)C2Cc3cccc(OC)c3OC2C1(C)C InChI: InChI=1S/C24H26O5/c1-24(2)22-15(11-13-7-5-9-17(26-3)20(13)28-22)19(25)16-12-14-8-6-10-18(27-4)21(14)29-23(16)24/h5-10,15-16,22-23H,11-12H2,1-4H3 Mass to charge: 393.16908 Retention Time: 11.92
113		NECA CHEBI ID: CHEBI:73284 PubChem ID: 448222 Chemical Formula: C12 H16 N6 O4 Smiles: CCNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O InChI: InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1 Mass to charge: 307.11664 Retention Time: 7.112
114		(2S,5aS,8aR)-1-Methyl-2-[3-(4-methyl-1-piperazinyl)-3-oxopropyl]-6-(1,2,3-thiadiazol-4-ylmethyl)octahydropyrrolo[3,2-E][1,4]diazepin-5(2H)-one CHEBI ID: NA PubChem ID: NA Chemical Formula: C19 H31 N7 O2 S Smiles: CN1CCN(C(=O)CC[C@H]2CNC(=O)[C@@H]3[C@@H](CCN3Cc3csnn3)N2C)CC1 InChI: InChI=1S/C19H31N7O2S/c1-23-7-9-25(10-8-23)17(27)4-3-15-11-20-19(28)18-16(24(15)2)5-6-26(18)12-14-13-29-22-21-14/h13,15-16,18H,3-12H2,1-2H3,(H,20,28)/t15-,16+,18-/m0/s1 Mass to charge: 422.23001 Retention Time: 8.242
115		2,2,6-TRIMETHYLCYCLOHEXANONE CHEBI ID: NA PubChem ID: 17000 Chemical Formula: C9 H16 O Smiles: CC1CCCC(C1=O)(C)C InChI: InChI=1S/C9H16O/c1-7-5-4-6-9(2,3)8(7)10/h7H,4-6H2,1-3H3 Mass to charge: 141.12665 Retention Time: 7.299
116		7-(2-aminophenyl)heptanoic acid CHEBI ID: CHEBI:190603 PubChem ID: 21656773 Chemical Formula: C13 H19 N O2 Smiles: C1=CC=C(C(=C1)CCCCCCC(=O)O)N InChI: InChI=1S/C13H19NO2/c14-12-9-6-5-8-11(12)7-3-1-2-4-10-13(15)16/h5-6,8-9H,1-4,7,10,14H2,(H,15,16) Mass to charge: 222.14754 Retention Time: 1.317
117		3,5-di-tert-Butyl-4-hydroxybenzaldehyde CHEBI ID: CHEBI:170060 PubChem ID: 73219 Chemical Formula: C15 H22 O2 Smiles: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=O InChI: InChI=1S/C15H22O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-9,17H,1-6H3 Mass to charge: 235.16791 Retention Time: 10.097
118		Prephenic acid CHEBI ID: CHEBI:16666 PubChem ID: 1028 Chemical Formula: C10 H10 O6 Smiles: C1=CC(C=CC1O)(CC(=O)C(=O)O)C(=O)O InChI: InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16) Mass to charge: 209.04338 Retention Time: 5.378
119		13,14-Dihydro-15-keto-tetranor prostaglandin F1α CHEBI ID: NA PubChem ID: NA Chemical Formula: C16 H28 O5 Smiles: CCCCCC(=O)CC[C@@H]1[C@@H](CCC(=O)O)[C@@H](O)C[C@H]1O InChI: InChI=1S/C16H28O5/c1-2-3-4-5-11(17)6-7-12-13(8-9-16(20)21)15(19)10-14(12)18/h12-15,18-19H,2-10H2,1H3,(H,20,21)/t12-,13-,14-,15+/m1/s1 Mass to charge: 299.1843 Retention Time: 8.33
120		N~6~-(2,3-Dihydroxybenzoyl)-N~2~-[(2,3-dihydroxyphenyl)(hydroxy)methyl]lysinamide CHEBI ID: NA PubChem ID: NA Chemical Formula: C20 H25 N3 O7 Smiles: NC(=O)C(CCCCNC(=O)c1cccc(O)c1O)NC(O)c1cccc(O)c1O InChI: InChI=1S/C20H25N3O7/c21-18(28)13(23-20(30)12-6-4-9-15(25)17(12)27)7-1-2-10-22-19(29)11-5-3-8-14(24)16(11)26/h3-6,8-9,13,20,23-27,30H,1-2,7,10H2,(H2,21,28)(H,22,29) Mass to charge: 418.16309 Retention Time: 6.33
121		2-(6-Hydroxyhexyl)-3-methylenesuccinic acid CHEBI ID: CHEBI:167766 PubChem ID: 23872059 Chemical Formula: C11 H18 O5 Smiles: C=C(C(CCCCCCO)C(=O)O)C(=O)O InChI: InChI=1S/C11H18O5/c1-8(10(13)14)9(11(15)16)6-4-2-3-5-7-12/h9,12H,1-7H2,(H,13,14)(H,15,16) Mass to charge: 229.10612 Retention Time: 6.717
122		5,7,11,19-tetraoxapentacyclo[10.8.0.0Â?,Âaâ°.0â´,â¸.0ÂaÂl,Âaâ¸]icosa-2(10),3,8,13,15,17-hexaen-16-ol CHEBI ID: NA PubChem ID: NA Chemical Formula: C16 H12 O5 Smiles: NA InChI: NA Mass to charge: 283.0592 Retention Time: 8.331
123		MTIC CHEBI ID: CHEBI:72568 PubChem ID: 76953 Chemical Formula: C5 H8 N6 O Smiles: CN=NNC1=C(NC=N1)C(=O)N InChI: InChI=1S/C5H8N6O/c1-7-11-10-5-3(4(6)12)8-2-9-5/h2H,1H3,(H2,6,12)(H,7,10)(H,8,9) Mass to charge: 227.09061 Retention Time: 6.91
124		(+)-myxothiazol A CHEBI ID: NA PubChem ID: 10972974 Chemical Formula: C25 H33 N3 O3 S2 Smiles: CC(C)C=CC=CC(C)C1=NC(=CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)N)OC)OC InChI: InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17-,18+,21-/m0/s1 Mass to charge: 488.20407 Retention Time: 10.777
125		(7S,13aS)-9,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium CHEBI ID: CHEBI:50540 PubChem ID: 5460122 Chemical Formula: C21 H24 N O4 Smiles: C[N+]12CCC3=CC4=C(C=C3C1CC5=C(C2)C(=C(C=C5)OC)OC)OCO4 InChI: InChI=1S/C21H24NO4/c1-22-7-6-14-9-19-20(26-12-25-19)10-15(14)17(22)8-13-4-5-18(23-2)21(24-3)16(13)11-22/h4-5,9-10,17H,6-8,11-12H2,1-3H3/q+1/t17-,22-/m0/s1 Mass to charge: 355.17566 Retention Time: 6.363
126		3,4-Dihydroxyphenylpropionic acid CHEBI ID: CHEBI:48400 PubChem ID: 348154 Chemical Formula: C9 H10 O4 Smiles: C1=CC(=C(C=C1CCC(=O)O)O)O InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13) Mass to charge: 181.05165 Retention Time: 5.522
127		Pioglitazone CHEBI ID: CHEBI:8228 PubChem ID: 4829 Chemical Formula: C19 H20 N2 O3 S Smiles: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3 InChI: InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23) Mass to charge: 355.10969 Retention Time: 10.044
128		3-O-(Carboxymethyl)estrone CHEBI ID: CHEBI:79692 PubChem ID: 225289 Chemical Formula: C20 H24 O4 Smiles: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OCC(=O)O InChI: InChI=1S/C20H24O4/c1-20-9-8-15-14-5-3-13(24-11-19(22)23)10-12(14)2-4-16(15)17(20)6-7-18(20)21/h3,5,10,15-17H,2,4,6-9,11H2,1H3,(H,22,23)/t15-,16-,17+,20+/m1/s1 Mass to charge: 327.16148 Retention Time: 8.099
129		S-Octylglutathione CHEBI ID: NA PubChem ID: 443115 Chemical Formula: C18 H33 N3 O6 S Smiles: CCCCCCCCSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N InChI: InChI=1S/C18H33N3O6S/c1-2-3-4-5-6-7-10-28-12-14(17(25)20-11-16(23)24)21-15(22)9-8-13(19)18(26)27/h13-14H,2-12,19H2,1H3,(H,20,25)(H,21,22)(H,23,24)(H,26,27)/t13-,14-/m0/s1 Mass to charge: 420.21439 Retention Time: 7.61
130		Dioctyldimethylammonium chloride CHEBI ID: CHEBI:183784 PubChem ID: 62581 Chemical Formula: C18 H39 N Smiles: CCCCCCCC[N+](C)(C)CCCCCCCC.[Cl-] InChI: InChI=1S/C18H40N.ClH/c1-5-7-9-11-13-15-17-19(3,4)18-16-14-12-10-8-6-2;/h5-18H2,1-4H3;1H/q+1;/p-1 Mass to charge: 270.31387 Retention Time: 9.939
131		Mitoxantrone CHEBI ID: CHEBI:50729 PubChem ID: 4212 Chemical Formula: C22 H28 N4 O6 Smiles: C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO InChI: InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2 Mass to charge: 557.18658 Retention Time: 8.861
132		Hydroxytyrosol CHEBI ID: CHEBI:68889 PubChem ID: 82755 Chemical Formula: C8 H10 O3 Smiles: C1=CC(=C(C=C1CCO)O)O InChI: InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2 Mass to charge: 372.14206 Retention Time: 6.864
133		brompheniramine CHEBI ID: CHEBI:3183 PubChem ID: 6834 Chemical Formula: C16 H19 Br N2 Smiles: CN(C)CCC(C1=CC=C(C=C1)Br)C2=CC=CC=N2 InChI: InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3 Mass to charge: 317.06436 Retention Time: 7.312
134		Azanidazole CHEBI ID: CHEBI:135001 PubChem ID: 6436171 Chemical Formula: C10 H10 N6 O2 Smiles: CN1C(=CN=C1C=CC2=NC(=NC=C2)N)[N+](=O)[O-] InChI: InChI=1S/C10H10N6O2/c1-15-8(13-6-9(15)16(17)18)3-2-7-4-5-12-10(11)14-7/h2-6H,1H3,(H2,11,12,14)/b3-2+ Mass to charge: 247.09503 Retention Time: 7.292
135		Cibarian CHEBI ID: CHEBI:3692 PubChem ID: 100275 Chemical Formula: C12 H18 N2 O12 Smiles: C(C[N+](=O)[O-])C(=O)OCC1C(C(C(C(O1)OC(=O)CC[N+](=O)[O-])O)O)O InChI: InChI=1S/C12H18N2O12/c15-7(1-3-13(20)21)24-5-6-9(17)10(18)11(19)12(25-6)26-8(16)2-4-14(22)23/h6,9-12,17-19H,1-5H2/t6-,9-,10+,11-,12+/m1/s1 Mass to charge: 381.08014 Retention Time: 6.183
136		7,8-dihydro-D-neopterin 2',3'-cyclic phosphate CHEBI ID: CHEBI:50972 PubChem ID: 135911932 Chemical Formula: C9 H12 N5 O6 P Smiles: C1C(OP(=O)(O1)O)C(C2=NC3=C(NC2)N=C(NC3=O)N)O InChI: InChI=1S/C9H12N5O6P/c10-9-13-7-5(8(16)14-9)12-3(1-11-7)6(15)4-2-19-21(17,18)20-4/h4,6,15H,1-2H2,(H,17,18)(H4,10,11,13,14,16)/t4-,6+/m1/s1 Mass to charge: 316.04419 Retention Time: 6.883
137		Cetiedil CHEBI ID: CHEBI:34619 PubChem ID: 66384 Chemical Formula: C20 H31 N O2 S Smiles: C1CCCN(CC1)CCOC(=O)C(C2CCCCC2)C3=CSC=C3 InChI: InChI=1S/C20H31NO2S/c22-20(23-14-13-21-11-6-1-2-7-12-21)19(18-10-15-24-16-18)17-8-4-3-5-9-17/h10,15-17,19H,1-9,11-14H2 Mass to charge: 348.20047 Retention Time: 8.967
138		Betulin CHEBI ID: CHEBI:3086 PubChem ID: 72326 Chemical Formula: C30 H50 O2 Smiles: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO InChI: InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1 Mass to charge: 460.41214 Retention Time: 14.045
139		12,13-Epoxytrichothec-9-ene CHEBI ID: NA PubChem ID: 162245 Chemical Formula: C15 H22 O2 Smiles: CC1=CC2C(CC1)(C3(CCC(C34CO4)O2)C)C InChI: InChI=1S/C15H22O2/c1-10-4-6-13(2)12(8-10)17-11-5-7-14(13,3)15(11)9-16-15/h8,11-12H,4-7,9H2,1-3H3/t11-,12-,13+,14-,15+/m1/s1 Mass to charge: 235.16808 Retention Time: 7.095
140		Dihydropteroic acid CHEBI ID: CHEBI:4581 PubChem ID: 135398662 Chemical Formula: C14 H14 N6 O3 Smiles: C1C(=NC2=C(N1)N=C(NC2=O)N)CNC3=CC=C(C=C3)C(=O)O InChI: InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21) Mass to charge: 359.11124 Retention Time: 7.467
141		Arsenous acid CHEBI ID: CHEBI:49900 PubChem ID: 545 Chemical Formula: H3 As O3 Smiles: O[As](O)O InChI: InChI=1S/AsH3O3/c2-1(3)4/h2-4H Mass to charge: 124.92243 Retention Time: 0.944
142		trovafloxacin CHEBI ID: CHEBI:9763 PubChem ID: 62959 Chemical Formula: C20 H15 F3 N4 O3 Smiles: C1C2C(C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F InChI: InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16? Mass to charge: 415.10065 Retention Time: 6.746
143		Hellebrigenin 3-acetate CHEBI ID: CHEBI:5644 PubChem ID: 267436 Chemical Formula: C26 H34 O7 Smiles: CC(=O)OC1CCC2(C3CCC4(C(CCC4(C3CCC2(C1)O)O)C5=COC(=O)C=C5)C)C=O InChI: InChI=1S/C26H34O7/c1-16(28)33-18-5-10-24(15-27)20-6-9-23(2)19(17-3-4-22(29)32-14-17)8-12-26(23,31)21(20)7-11-25(24,30)13-18/h3-4,14-15,18-21,30-31H,5-13H2,1-2H3/t18-,19+,20-,21+,23+,24-,25-,26-/m0/s1 Mass to charge: 522.24585 Retention Time: 8.343
144		11H-Benzofuro(3,2-b)(1)benzopyran-11-one, 2-(5,6-dihydro-9-hydroxy-2-methyl-2,6-methano-2H-1-benzoxocin-4-yl)-5a,10a-dihydro-1,3,5a,8-tetrahydroxy-10a-(3-methyl-2-butenyl)- CHEBI ID: NA PubChem ID: 157791 Chemical Formula: C33 H30 O9 Smiles: CC(=CCC12C(=O)C3=C(C=C(C(=C3O)C4=CC5(CC(C4)C6=C(O5)C=C(C=C6)O)C)O)OC1(C7=C(O2)C=C(C=C7)O)O)C InChI: InChI=1S/C33H30O9/c1-16(2)8-9-32-30(38)28-26(42-33(32,39)22-7-5-20(35)12-25(22)41-32)13-23(36)27(29(28)37)18-10-17-14-31(3,15-18)40-24-11-19(34)4-6-21(17)24/h4-8,11-13,15,17,34-37,39H,9-10,14H2,1-3H3 Mass to charge: 569.18207 Retention Time: 6.935
145		LSD-d3 CHEBI ID: NA PubChem ID: 46782093 Chemical Formula: C20 H22 [2]H3 N3 O Smiles: CCN(CC)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C InChI: InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1/i3D3 Mass to charge: 327.22733 Retention Time: 10.426
146		1a-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-7a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione CHEBI ID: NA PubChem ID: NA Chemical Formula: C21 H24 O3 Smiles: CC(C)=CCC/C(C)=C/CC12OC1(C)C(=O)c1ccccc1C2=O InChI: InChI=1S/C21H24O3/c1-14(2)8-7-9-15(3)12-13-21-19(23)17-11-6-5-10-16(17)18(22)20(21,4)24-21/h5-6,8,10-12H,7,9,13H2,1-4H3/b15-12+ Mass to charge: 323.16629 Retention Time: 10.667
147		Senkyunolide A CHEBI ID: CHEBI:194178 PubChem ID: 3085257 Chemical Formula: C12 H16 O2 Smiles: CCCCC1C2=C(C=CCC2)C(=O)O1 InChI: InChI=1S/C12H16O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,11H,2-4,6,8H2,1H3/t11-/m0/s1 Mass to charge: 193.12132 Retention Time: 8.974
148		(Z)-N-[(2S)-2-{(Z)-[(2S,3S,6R,7S)-2,3-Diamino-1,6,7-trihydroxy-8-{1-[hydroxy(imino)methyl]-2-imino-4-imidazolidinyl}octylidene]amino}-1-hydroxypropylidene]-L-valine CHEBI ID: NA PubChem ID: NA Chemical Formula: C20 H38 N8 O7 Smiles: CC(C)[C@H](N=C(O)[C@H](C)N=C(O)[C@@H](N)[C@@H](N)CC[C@@H](O)[C@@H](O)CC1CN(C(=N)O)C(=N)N1)C(=O)O InChI: InChI=1S/C20H38N8O7/c1-8(2)15(18(33)34)27-16(31)9(3)25-17(32)14(22)11(21)4-5-12(29)13(30)6-10-7-28(20(24)35)19(23)26-10/h8-15,29-30H,4-7,21-22H2,1-3H3,(H2,23,26)(H2,24,35)(H,25,32)(H,27,31)(H,33,34)/t9-,10?,11-,12+,13-,14-,15-/m0/s1 Mass to charge: 483.26999 Retention Time: 8.533
149		Tinabinol CHEBI ID: CHEBI:177684 PubChem ID: 65443 Chemical Formula: C23 H34 O2 S Smiles: CCCCCC(C)C(C)C1=CC(=C2C3=C(C(OC2=C1)(C)C)SCCC3)O InChI: InChI=1S/C23H34O2S/c1-6-7-8-10-15(2)16(3)17-13-19(24)21-18-11-9-12-26-22(18)23(4,5)25-20(21)14-17/h13-16,24H,6-12H2,1-5H3 Mass to charge: 373.22061 Retention Time: 10.126
150		Algestone CHEBI ID: CHEBI:763 PubChem ID: 11687 Chemical Formula: C21 H30 O4 Smiles: CC(=O)C1(C(CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O)O InChI: InChI=1S/C21H30O4/c1-12(22)21(25)18(24)11-17-15-5-4-13-10-14(23)6-8-19(13,2)16(15)7-9-20(17,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16+,17+,18-,19+,20+,21-/m1/s1 Mass to charge: 347.22052 Retention Time: 9.287
151		terpendole J CHEBI ID: CHEBI:66209 PubChem ID: 9984208 Chemical Formula: C32 H43 N O5 Smiles: CC(=CCOC(C)(C)C1C(C2C3(O2)C(O1)CCC4(C3(CCC5C4(C6=C(C5)C7=CC=CC=C7N6)C)O)C)O)C InChI: InChI=1S/C32H43NO5/c1-18(2)13-16-36-28(3,4)26-24(34)27-32(38-27)23(37-26)12-14-29(5)30(6)19(11-15-31(29,32)35)17-21-20-9-7-8-10-22(20)33-25(21)30/h7-10,13,19,23-24,26-27,33-35H,11-12,14-17H2,1-6H3/t19-,23-,24+,26-,27+,29+,30+,31-,32-/m0/s1 Mass to charge: 520.30939 Retention Time: 9.621
152		diethyl oxalpropionate CHEBI ID: NA PubChem ID: NA Chemical Formula: C9 H14 O5 Smiles: CCOC(=O)C(=O)C(C)C(=O)OCC InChI: InChI=1S/C9H14O5/c1-4-13-8(11)6(3)7(10)9(12)14-5-2/h6H,4-5H2,1-3H3 Mass to charge: 201.07612 Retention Time: 12.207
153		L-(-)-Serine CHEBI ID: CHEBI:17115 PubChem ID: 5951 Chemical Formula: C3 H7 N O3 Smiles: C(C(C(=O)O)N)O InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 Mass to charge: 106.04967 Retention Time: 0.804

Study Data

MS Study

Project

Study

Sample (Total Count:2)

Mass Spectrometry

Author List

File Details

Metabolites/Compounds

Cetrimonium

Berberine

(15Z)-9,12,13-Trihydroxy-15-octadecenoic acid

Protopine

(5R,6S)-5-Hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one

4-morpholinobenzoic acid

Corchorifatty acid F

Caprolactam

1-phenyl-N-(6-quinoxalinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide

16-Hydroxyhexadecanoic acid

Sorbic acid

9-Oxo-10(E),12(E)-octadecadienoic acid

13(S)-HOTrE

Ostruthin

Luteolin

5-Hydroxyindole-3-acetic acid

1-(4-Methylphenyl)pyrrolidine-2,5-dione

Myristyl sulfate

Apigenin

3-(1,1,2,3,3,3-hexafluoropropyl)adamantane-1-carboxylic acid

phenothiazine

(+/-)9-HpODE

Phloionolic acid

1-{2-[(4-fluorophenyl)sulfonyl]ethyl}-4-(2-pyridinyl)piperazine

3-Pyridylacetic acid

aspoquinolone A

ethyl 3-[(1-benzyl-4-piperidyl)amino]-2-cyanoacrylate

Linoleoyl Ethanolamide

3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

4-Pyridineacetic acid

Payzone

Dibutyl sebacate

(3aR,7aS,8S,9aR)-5,8-dimethyl-3-methylidene-2H,3H,3aH,4H,6H,7H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione

Menadione

Dibutyl phthalate

4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Carbofuran

[1,1'-biphenyl]-2,2'-dicarboxylic acid

3-tert-Butyladipic acid

(2E)-3-(4-Acetoxy-2,3-dihydroxy-2,5,5,8a-tetramethyldecahydro-1-naphthalenyl)acrylic acid

1,4-Bis(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan

(+/-)12(13)-DiHOME

Tridemorph

1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one

Tangeritin

ethyl 4-{[4-(tert-butyl)anilino]sulfonyl}-5-(4-chlorophenyl)-2-methyl-3-furoate

(2S)-2-Amino-4-hexynoic acid

N-tert-Butyloxycarbonyl-deacetyl-leupeptin

AM-Toxin I

2-[(3S)-1-(4-Chlorobenzyl)-3-pyrrolidinyl]-5-(trifluoromethyl)-1H-benzimidazole

3-Phenylpropanoic acid

N1-(1-Phenylethyl)-3,4,5-trimethoxybenzamide

Matairesinol

Dioscin

L-Tyrosine

3,8,9-trihydroxy-10-propyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one

6-Acetylcodeine

1-{3-[3,5-di(trifluoromethyl)phenyl]prop-2-ynyl}piperidine hydrochloride

2,3-Dinor-8-epi-prostaglandin F2α

alanycarb

Nobiletin

Oleamide

N-Benzyl-N-methyl-2-[(3R,4S)-3-({5-[(phenylsulfanyl)methyl]-1,2-oxazol-3-yl}methyl)-4-piperidinyl]acetamide

N-(2-{4-[5-(Acetylamino)-1H-benzimidazol-2-yl]phenyl}-1H-benzimidazol-5-yl)acetamide

5-[4-(3-hydroxy-4-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

Asarone

8-{3-Oxo-2-[(2E)-2-penten-1-yl]-1-cyclopenten-1-yl}octanoic acid

(E)-Dacarbazine

Ectocarpene

salirasib

Cuminaldehyde

5,7,11,19-tetraoxapentacyclo[10.8.0.0Â?,Âaâ°.0â´,â¸.0ÂaÂl,Âaâ¸]icosa-2(10),3,8,13,15,17-hexaen-16-ol