#METABOLOMICS WORKBENCH jord001_20250201_151607 DATATRACK_ID:5587 STUDY_ID:ST003998 ANALYSIS_ID:AN006592 PROJECT_ID:PR002503
VERSION             	1
CREATED_ON             	June 23, 2025, 4:27 pm
#PROJECT
PR:PROJECT_TITLE                 	Untargeted Metabolomics and In silico Screening of Sisymbrium officinale:
PR:PROJECT_TITLE                 	Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents
PR:PROJECT_SUMMARY               	Sisymbrium officinale (SO), often referred to as "the plant of singers," is a
PR:PROJECT_SUMMARY               	revered traditional Mediterranean medicinal herb known for its applications in
PR:PROJECT_SUMMARY               	treating inflammatory diseases. Despite its historical use, comprehensive
PR:PROJECT_SUMMARY               	metabolomics and in silico studies validating its anti-inflammatory effects
PR:PROJECT_SUMMARY               	remain scarce. The study reported here seeks to uncover and characterize the
PR:PROJECT_SUMMARY               	bioactive compounds within SO, providing a critical step in identifying
PR:PROJECT_SUMMARY               	potential anti-inflammatory agents. To achieve this, we extracted plant
PR:PROJECT_SUMMARY               	compounds using various solvents with differing polarities, i.e., water,
PR:PROJECT_SUMMARY               	methanol, ethanol, acetone, and chloroform. These extractions were followed by
PR:PROJECT_SUMMARY               	phase separation (polar phase and nonpolar phase) of crude extracts.
PR:PROJECT_SUMMARY               	Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase)
PR:PROJECT_SUMMARY               	spectroscopy to obtain a preliminary quantification of the diverse functional
PR:PROJECT_SUMMARY               	groups in the SO extracts.We also carried out inflammatory bioassay analysis
PR:PROJECT_SUMMARY               	followed by chemometrics and in silico screening.
PR:INSTITUTE                     	King Abdullah University of Science and Technology
PR:LAST_NAME                     	Kahfi
PR:FIRST_NAME                    	Jordan
PR:ADDRESS                       	Thuwal, Thuwal, Makkah, 23955, Saudi Arabia
PR:EMAIL                         	jordan.kahfi@kaust.edu.sa
PR:PHONE                         	0541244806
#STUDY
ST:STUDY_TITLE                   	Untargeted Metabolomics and In silico Screening of Sisymbrium officinale:
ST:STUDY_TITLE                   	Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents
ST:STUDY_SUMMARY                 	Sisymbrium officinale (SO), often referred to as "the plant of singers," is a
ST:STUDY_SUMMARY                 	revered traditional Mediterranean medicinal herb known for its applications in
ST:STUDY_SUMMARY                 	treating inflammatory diseases. Despite its historical use, comprehensive
ST:STUDY_SUMMARY                 	metabolomics and in silico studies validating its anti-inflammatory effects
ST:STUDY_SUMMARY                 	remain scarce. The study reported here seeks to uncover and characterize the
ST:STUDY_SUMMARY                 	bioactive compounds within SO, providing a critical step in identifying
ST:STUDY_SUMMARY                 	potential anti-inflammatory agents. To achieve this, we extracted plant
ST:STUDY_SUMMARY                 	compounds using various solvents with differing polarities, i.e., water,
ST:STUDY_SUMMARY                 	methanol, ethanol, acetone, and chloroform. These extractions were followed by
ST:STUDY_SUMMARY                 	phase separation (polar phase and nonpolar phase) of crude extracts.
ST:STUDY_SUMMARY                 	Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase)
ST:STUDY_SUMMARY                 	spectroscopy to obtain a preliminary quantification of the diverse functional
ST:STUDY_SUMMARY                 	groups in the SO extracts. GC-MS analysis resulted in the identification of SO
ST:STUDY_SUMMARY                 	primary metabolites including sugars (rhamnose, trehalose, fructopyranose,
ST:STUDY_SUMMARY                 	myo-inositol, etc.), amino acids (glycine, lysine, valine, etc.), and fatty
ST:STUDY_SUMMARY                 	acids (linolenic acid, norlinolenic acid, aminovaleric acid, etc.). The LC-MS
ST:STUDY_SUMMARY                 	analysis of both polar and nonpolar fraction resulted in diverse secondary
ST:STUDY_SUMMARY                 	metabolite groups including alkaloids (tetramethylpyrazine, pilocarpine),
ST:STUDY_SUMMARY                 	flavonoids (apigetrin, cynaroside, vitexin 4-O-glucoside, kaempferol, galangin,
ST:STUDY_SUMMARY                 	naringenin, etc.), and plant sterols (zymosterol). The bioassay analysis showed
ST:STUDY_SUMMARY                 	that methanol, ethanol, and acetone possess the highest anti-inflammatory
ST:STUDY_SUMMARY                 	activity through NO suppresion of RAW 264.7 macrophage cells. Further,
ST:STUDY_SUMMARY                 	chemometrics and in silico screening (molecular docking and ADMET) resulted in
ST:STUDY_SUMMARY                 	two flavonoid glycosides, apigetrin and 3-O-α-L-arabinopyranoside, as potential
ST:STUDY_SUMMARY                 	anti-inflammatory compounds that suppress the activity of human inducible NO
ST:STUDY_SUMMARY                 	synthase (iNOS, PDB ID: 3E7G), endothelial NOS (eNOS, PDB ID: 6AV7), and
ST:STUDY_SUMMARY                 	neuronal NOS (nNOS, PDB ID: 6CID). These findings pave the ways for further
ST:STUDY_SUMMARY                 	validation studies including isolation, purification, in vitro, and in vivo
ST:STUDY_SUMMARY                 	analysis.
ST:INSTITUTE                     	King Abdullah University of Science and Technology
ST:LAST_NAME                     	Kahfi
ST:FIRST_NAME                    	Jordan
ST:ADDRESS                       	Thuwal, Thuwal, Makkah, 23955, Saudi Arabia
ST:EMAIL                         	jordan.kahfi@kaust.edu.sa
ST:PHONE                         	0541244806
#SUBJECT
SU:SUBJECT_TYPE                  	Plant
SU:SUBJECT_SPECIES               	Sisymbrium officinale
SU:TAXONOMY_ID                   	203582
#FACTORS
#SUBJECT_SAMPLE_FACTORS:         	SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data
SUBJECT_SAMPLE_FACTORS           	-	A1	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=A1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A1-NP
SUBJECT_SAMPLE_FACTORS           	-	A2	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=A2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A2-NP
SUBJECT_SAMPLE_FACTORS           	-	A3	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=A3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A3-NP
SUBJECT_SAMPLE_FACTORS           	-	A4	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=A4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A4-NP
SUBJECT_SAMPLE_FACTORS           	-	A5	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=A5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A5-NP
SUBJECT_SAMPLE_FACTORS           	-	C1	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=C1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C1-NP
SUBJECT_SAMPLE_FACTORS           	-	C2	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=C2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C2-NP
SUBJECT_SAMPLE_FACTORS           	-	C3	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=C3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C3-NP
SUBJECT_SAMPLE_FACTORS           	-	C4	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=C4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C4-NP
SUBJECT_SAMPLE_FACTORS           	-	C5	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=C5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C5-NP
SUBJECT_SAMPLE_FACTORS           	-	E1	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=E1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E1-NP
SUBJECT_SAMPLE_FACTORS           	-	E2	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=E2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E2-NP
SUBJECT_SAMPLE_FACTORS           	-	E3	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=E3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E3-NP
SUBJECT_SAMPLE_FACTORS           	-	E4	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=E4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E4-NP
SUBJECT_SAMPLE_FACTORS           	-	E5	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=E5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E5-NP
SUBJECT_SAMPLE_FACTORS           	-	M1	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=M1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M1-NP
SUBJECT_SAMPLE_FACTORS           	-	M2	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=M2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M2-NP
SUBJECT_SAMPLE_FACTORS           	-	M3	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=M3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M3-NP
SUBJECT_SAMPLE_FACTORS           	-	M4	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=M4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M4-NP
SUBJECT_SAMPLE_FACTORS           	-	M5	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=M5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M5-NP
SUBJECT_SAMPLE_FACTORS           	-	W1	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=W1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W1-NP
SUBJECT_SAMPLE_FACTORS           	-	W2	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=W2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W2-NP
SUBJECT_SAMPLE_FACTORS           	-	W3	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=W3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W3-NP
SUBJECT_SAMPLE_FACTORS           	-	W4	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=W4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W4-NP
SUBJECT_SAMPLE_FACTORS           	-	W5	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=W5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W5-NP
#COLLECTION
CO:COLLECTION_SUMMARY            	The leaf sample was collected from wild Sisymbrium officinale Plant grown in in
CO:COLLECTION_SUMMARY            	the mountainous regions of Hebron, Palestine in February 2023.
CO:SAMPLE_TYPE                   	Leaves
#TREATMENT
TR:TREATMENT_SUMMARY             	Sisymbrium officinale leaves were lyophilized and extracted with different type
TR:TREATMENT_SUMMARY             	of solvent (water, ethanol, methanol, acetone, and chloroform). The dried crude
TR:TREATMENT_SUMMARY             	extracts were subjected for liquid-liquid phase separation: polar phase and
TR:TREATMENT_SUMMARY             	nonpolar phase prior GC-MS and LC-MS analysis
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	SO powder (25 mg) was mixed with 2.0 mL of each different solvent: water,
SP:SAMPLEPREP_SUMMARY            	methanol, ethanol, ethyl acetate, and acetone. The mixtures were sonicated in
SP:SAMPLEPREP_SUMMARY            	ice bath (15 minutes) to avoid excessive heating, macerated on a shaker
SP:SAMPLEPREP_SUMMARY            	overnight (25 °C, 1400 rpm, 17 hours) to ensure maximum extraction, and
SP:SAMPLEPREP_SUMMARY            	centrifuged (25 °C, 14,000X g, 10 minutes) to separate the debris and extracted
SP:SAMPLEPREP_SUMMARY            	materials. The supernatant was transferred into new labelled tubes (water,
SP:SAMPLEPREP_SUMMARY            	methanol, ethanol, ethyl acetate, and acetone) and stored at -20 °C.
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_SUMMARY        	The nonpolar phase measurement was performed using Thermo Vanquish. UPLC BEH C18
CH:CHROMATOGRAPHY_SUMMARY        	column (2.1 × 10mm, 1.7µm) with a flow rate of 0.4 mL/min. Two solutions were
CH:CHROMATOGRAPHY_SUMMARY        	used for the mobile phase, namely Solution A (60% acetonitrile/40% water; 0.1%
CH:CHROMATOGRAPHY_SUMMARY        	formic acid; 10mM ammonium formate) and Solution B (10% acetonitrile/90%
CH:CHROMATOGRAPHY_SUMMARY        	isopropanol; 0.1% formic acid; 10mM ammonium formate).
CH:CHROMATOGRAPHY_TYPE           	Reversed phase
CH:INSTRUMENT_NAME               	Thermo Vanquish
CH:COLUMN_NAME                   	Waters ACQUITY UPLC BEH C18 (100 x 2.1mm,1.7um)
CH:SOLVENT_A                     	60% acetonitrile/40% water; 0.1% formic acid; 10mM ammonium formate
CH:SOLVENT_B                     	10% acetonitrile/90% isopropanol; 0.1% formic acid; 10mM ammonium formate
CH:FLOW_GRADIENT                 	The gradient was changed as follow: 0-2 minutes, 43% B; 2-18 minutes, from 43% B
CH:FLOW_GRADIENT                 	to 99% B; 18-20 minutes, 99%B; 20-22 minutes, from 99% B to 43% B.
CH:FLOW_RATE                     	0.4 mL/min
CH:COLUMN_TEMPERATURE            	55°C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Bruker timsTOF PRO
MS:INSTRUMENT_TYPE               	QTOF
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	POSITIVE
MS:MS_COMMENTS                   	The Bruker timsTOF PRO was used. This instrument was operated using following
MS:MS_COMMENTS                   	parameters: the end plate offset voltage was 500V, capillary voltage was 4500V,
MS:MS_COMMENTS                   	nebulizer pressure was 2.2 Bar, dry gas flow was 10 L/min, and dry gas
MS:MS_COMMENTS                   	temperature was 220°C. The MS scan ranged between 100–1350 m/z. For the ion
MS:MS_COMMENTS                   	mobility detector, the 1/K0 scan ranged between 0.55–1.83V s/cm2, ramp time
MS:MS_COMMENTS                   	was 100ms, accumulation time was 100ms, and ramp rate was 9.42 Hz.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	AUC
MS_METABOLITE_DATA_START
Samples	A1	A2	A3	A4	A5	C1	C2	C3	C4	C5	E1	E2	E3	E4	E5	M1	M2	M3	M4	M5	W1	W2	W3	W4	W5
Factors	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract
.gamma.-Linolenoyl ethanolamide	119712	142443	121622	137422	118189	137050	152865	124891	151487	123416	147592	115415	102740	132068	131970	131266	177201	117802	132973	119569	48	6593	0	5537	6600
1,2-Dioleoyl-sn-glycero-3-phospho-rac-1-glycerol	0	0	4769	4303	0	0	0	0	0	0	5266	6672	3696	4439	4579	4448	8538	6385	7850	7256	314	399	252	0	484
1-Hydroxy vitamin D3	12017	8926	8998	9701	9624	8624	12341	7997	8625	8044	11313	10554	8269	10122	10503	10299	14664	11141	12623	11964	1726	0	1477	0	978
1-Monolinolenin	434028	379383	407405	372218	436129	203108	207472	183179	240636	154841	517319	507208	330151	532693	488887	398325	624220	489173	481352	449157	0	0	0	0	0
1-Palmitoyl-2-oleoyl-phosphatidylglycerol	9578	8808	8426	7271	8942	767	0	0	0	0	12845	11294	8051	10390	9149	9479	17653	12371	14739	12672	1184	0	969	861	760
3-Hydroxy-2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	23699	19453	34115	31578	23893	12981	0	0	0	0	25951	29908	17104	21790	23982	32281	205099	29398	21649	22256	0	0	0	0	0
5-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)phenyl beta-D-glucopyranoside	6672	7164	6608	6015	7454	0	0	0	2449	0	10507	7160	8327	8454	8330	7275	9180	6465	7771	6907	0	0	0	0	0
6''-O-malonylgenistin	12830	9497	15047	9872	9268	0	0	0	1866	0	11065	12408	8037	10772	8106	9250	10033	10207	9773	10371	3469	2963	0	4536	3805
7-α-Hydroxy-4-cholesten-3-one	3070	2658	2230	2134	2685	5385	4817	4275	3354	3825	2975	2084	1646	2536	3323	3511	4045	3699	3644	2287	0	0	0	0	0
9-Oxo-10(E),12(E)-octadecadienoic acid	181635	179545	134965	146357	147152	102374	160610	111957	134308	103864	202578	221241	150549	208313	207174	211086	237591	230199	218122	214317	161218	213870	89373	212282	197851
Apigenin	1205518	1109472	1009468	1026545	1091972	435760	596438	510402	616884	314645	1212247	1243260	992926	1205289	1230366	1102613	1422398	1129616	1286739	1110148	214214	318120	29439	272384	332387
Butorphanol	27580	25965	21010	0	23146	0	0	0	0	0	15605	22220	15017	18867	15076	44414	32762	27722	47938	28207	16746	22110	21627	32015	24510
Cer 18:0;3O/16:0;(2OH)	42143	0	0	26310	0	16446	16561	13433	16085	9794	44011	45169	26406	46620	40087	35781	55660	38619	47710	42813	0	0	0	0	0
Cer 18:1;3O/16:0;(2OH)	47677	38397	42282	36922	43050	23496	24758	19310	21693	15742	51226	51303	30509	51885	44380	39950	66623	45193	54566	49169	0	783	0	69	78
Cer 26:0;2O/20:0	6929	4725	3273	5137	5571	2604	4671	3326	4921	3714	5726	3841	3377	4947	5206	3431	4151	3249	3012	4530	584	987	0	533	1157
Chrysanthemin	5520	3486	3297	4611	0	0	0	0	981	0	10443	13630	12070	15708	13605	17450	19344	16524	13638	11681	0	0	0	0	0
Di(2-nonyl) phthalate	22754	0	27356	24343	0	22390	22165	21847	25974	21523	29648	0	21939	0	26430	20795	24677	0	21595	23295	0	0	0	0	0
Dilauryl thiodipropionate	16470	21522	10641	15636	19829	14012	6650	10265	14468	15879	16173	13737	8037	11795	12952	19254	15767	9394	8026	15149	36791	16254	11751	15124	16085
Dioctyl phthalate	10954	19164	15038	15190	24762	77770	31223	20414	23433	23195	22481	21072	17427	17440	24183	12440	22153	15150	19898	14961	7227	5746	6217	8488	6359
Ergosterol peroxide	44721	38925	41419	39427	44880	44890	43148	28797	39656	22359	53442	50272	27217	57612	44228	53491	92713	57030	59119	71304	1173	2266	360	2444	2419
Erucamide	73353	323885	144171	75025	207532	107047	212737	152915	123255	122893	163780	114244	153411	129728	76543	201996	180003	158918	195109	177012	169557	105292	100145	105121	95622
LPC 16:0-SN2	92706	86003	102991	70073	58987	0	0	0	0	0	94826	110624	62791	92491	83620	95468	446790	108184	97164	89870	804	0	0	3070	0
LPC 18:1-SN2	29359	27106	26562	21380	15578	0	0	0	0	0	27862	24574	18042	18468	26320	27377	140589	31483	23487	21878	0	0	3011	0	0
Lupenone	4205	3252	3485	3098	3535	4514	4102	3398	2923	2166	3686	3449	2252	3425	3401	3084	4850	3433	3562	3945	0	0	310	0	0
N,N-dimethyldodecylamine N-oxide	242623	201251	189671	146367	217571	243034	330338	194978	205331	119947	185345	225428	158226	260550	237725	147041	243608	208033	211178	162001	36753	32083	29400	25834	27984
N-nervonoyl-D-erythro-sphinganine	5975	8557	6250	5207	8846	0	4762	2978	4815	0	11711	6464	4503	9627	5019	7203	6083	7014	5344	5069	0	0	0	0	0
N-octylsphingosine	757	266	386	284	650	1344	1898	1865	2932	1803	797	516	442	716	560	760	867	707	729	910	0	0	0	0	0
N-palmitoylsphingosine	3940	3540	3918	3191	3714	2370	3211	2450	2719	2144	4248	4514	3026	4736	3753	4060	5398	3893	4778	3767	0	273	0	256	257
PC 16:0_16:0	5372	4254	4285	4404	5056	1114	775	817	1634	0	9112	6240	3627	7075	5880	4800	8998	5943	6369	5656	568	650	570	643	681
PC 16:0_18:3	199616	160841	165179	156549	184588	15678	10417	11422	27038	11801	264713	227794	110067	243217	170240	109709	244242	178894	174509	125350	245	778	0	1300	721
PC 18:0_14:1	72887	59382	61286	52938	56592	9694	0	9896	11274	5581	65842	64047	39264	52228	50514	45041	85748	53352	69213	53919	1222	3216	0	1244	2812
PC 18:0_16:2	61434	47290	49474	47862	61815	12887	11597	11929	16915	8480	55510	64843	40742	62090	55039	44628	76888	54474	58229	47608	5029	4624	4428	5994	5802
PC 18:0_18:2	4756	4778	4535	3783	4507	0	875	789	1167	545	5983	5332	2714	5725	3975	3079	7861	4388	4811	3765	0	33	0	0	0
PC 18:1_18:3	31128	26098	25462	22908	26688	4466	3867	3283	6451	3325	34784	33358	16439	31384	26432	18821	43638	27404	27228	20374	1083	968	984	1342	1281
PC 18:2_16:4	98406	103248	83072	80147	108443	12473	13762	9691	25577	10131	138171	128831	57881	137518	99154	63681	117126	94948	82142	53241	0	1564	0	0	0
PC 18:2_18:3	58837	48911	48148	45729	53641	7406	6227	6251	10761	5070	69019	67776	32272	66554	51961	33906	72898	53766	49199	36836	245	793	0	504	729
PC 18:3_18:3	185767	149929	157122	142206	173719	23812	17828	13291	33597	15702	243069	216257	99981	222210	163943	107753	234240	169775	151440	115293	2386	2724	1405	5125	3954
PC 20:0_14:1165245428	13480	11302	11530	11702	12011	2256	1976	2394	2989	1894	16327	15073	8237	13497	11215	9460	19878	12056	13291	9718	1253	1379	1150	1500	1623
PE 15:0_17:1	17948	17522	17063	19898	23122	2005	1701	2623	1500	2681	23628	23452	19025	17289	17013	18874	33123	23502	25198	26068	0	0	0	0	3580
PE 16:0_16:1	104401	73695	87583	93110	99243	18408	0	0	0	19024	178637	165804	107230	112129	100076	82725	186280	126120	83243	135447	48118	38547	42046	50321	48790
PE 17:1_17:1	58834	42204	46315	52620	51424	0	0	3692	0	12992	97391	88321	59661	57142	53149	44308	123037	71926	48346	79168	33457	27642	29807	35407	33177
Pelargonidin 3-O-glucoside	1487262	1342120	1342349	1224562	1321349	63595	49288	41333	409633	75388	1326020	1242691	1110800	1400744	1191008	1127516	1322589	1235105	1269132	1219259	81796	43816	83030	46295	48266
Pelargonin	21337	21922	19860	18463	21390	0	0	0	6272	0	26879	27184	22475	23611	24174	23068	25215	23716	27303	24125	0	0	0	0	0
Pheophorbide A	5346009	4396297	4317066	3676243	2967090	776606	774238	670029	1945396	663124	5262875	5876491	3639576	6364325	6030555	1478305	1763507	1178290	1208134	1280986	228948	181907	205759	231405	225936
Sphingosine	38317	36000	30284	24619	40211	36498	39739	30684	54898	28456	49120	37505	24753	43340	42799	39050	52430	30056	25773	0	3006	6464	1197	8892	8326
Stearic acid ethyl ester	555	492	520	242	501	3044	3462	2346	2724	2688	2128	2566	1944	3262	2334	202	607	0	0	488	0	0	0	0	0
Tetrahydrodicranenone B	838736	783067	701673	480949	910300	643078	730246	586416	722591	575175	714890	884032	596475	969840	745963	531156	864332	801987	665007	708425	209051	212841	100032	274418	216777
TG 16:0_18:3_18:3	125552	117650	125942	126118	100490	145443	128556	153360	165224	154620	128900	103996	147791	112625	130581	142811	115164	145138	157573	141065	52115	47560	41481	41863	41693
TG 16:3_16:3_18:3	101554	106964	109452	136419	117184	104299	64425	79424	111231	108050	97812	111785	137078	111465	91397	125559	89895	125742	102693	134031	26738	8408	26154	14083	7175
TG 18:0_18:3_18:3	106725	117901	108888	111471	117286	73195	51771	60356	72958	65559	101676	112842	121866	105106	110540	120913	117026	118544	130284	119774	0	5762	0	0	4366
TG 18:3_18:3_18:3	134628	145123	140072	133974	142886	153093	142400	161748	156946	193136	137349	118550	166655	160379	138140	152653	123743	139446	151228	146790	68095	67768	54425	69767	60636
Triphenylphosphine oxide	3143	2337	5259	6102	3988	495184	5561	7028	4067	7511	3525	1473	0	0	0	2178	1200	4003	0	0	6600	1482	5766	1617	1806
Vitamin K1	173976	143055	137103	128059	153722	79080	70568	61863	74897	53196	169159	161323	96287	173807	144766	117503	211615	150657	145262	145678	3602	3855	2972	4075	3729
Vitamin K1 2,3-epoxide	5638	4167	4412	3815	5326	1912	2194	1714	2254	1081	5095	4468	2516	6612	4495	4019	7491	4548	4396	4383	0	0	0	0	0
Vitexin 4-O-glucoside	6820	6376	6223	5225	6433	0	0	0	725	0	6923	5855	4081	6661	6959	5728	6124	7366	6281	6319	0	0	0	0	0
Zymosterol	57205	49011	48291	45853	53558	47591	58487	47501	45247	34147	50041	56280	33991	55630	46469	45081	70215	53430	57464	51604	3549	4046	2648	4630	4265
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	Molecular Formula	RT [min]	M meas.	Δm/z [ppm]	Pubchem CID	INCHI_KEY
.gamma.-Linolenoyl ethanolamide	C20H35NO2	0.78	321.2666	-0.652	78382209 	KRDUNUMTOBLEPM-UHFFFAOYSA-N
1,2-Dioleoyl-sn-glycero-3-phospho-rac-1-glycerol	C42H79O10P	7.21	774.541	-0.103	11846228 	DSNRWDQKZIEDDB-GCMPNPAFSA-N
1-Hydroxy vitamin D3	C27H44O2	1.78	400.3338	-0.811	5284515 	OFHCOWSQAMBJIW-GITLSTMWSA-N 
1-Monolinolenin	C21H36O4	0.8	352.2612	-0.443	5872092 	GGJRAQULURVTAJ-IUQGRGSQSA-N 
1-Palmitoyl-2-oleoyl-phosphatidylglycerol	C40H77O10P	7.16	748.5251	-0.43	5283509  	PAZGBAOHGQRCBP-DDDNOICHSA-N  
3-Hydroxy-2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	C26H50NO7P	0.73	519.3321	-0.72	24871190 	LSUXCWJOIAWGOU-UTJQPWESSA-N 
5-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)phenyl beta-D-glucopyranoside	C22H22O11	0.57	462.1161	-0.308	11751616	OVSQVDMCBVZWGM-HBDJNLTOSA-N
6''-O-malonylgenistin	C24H22O13	0.58	518.1058	-0.434	44257280	FRAUJUKWSKMNJY-RSEYPYQYSA-N
7-α-Hydroxy-4-cholesten-3-one	C27H44O2	2.53	400.3341	-0.127	123743	IOIZWEJGGCZDOL-RQDYSCIWSA-N
9-Oxo-10(E),12(E)-octadecadienoic acid	C18H30O3	0.72	294.2192	-1.003	5283011  	LUZSWWYKKLTDHU-SIGMCMEVSA-N  
Apigenin	C15H10O5	0.64	270.0534	2.11	5280443	KZNIFHPLKGYRTM-UHFFFAOYSA-N
Butorphanol	C21H29NO2	0.74	327.2201	0.672	5361092	IFKLAQQSCNILHL-QHAWAJNXSA-N
Cer 18:0;3O/16:0;(2OH)	C34H69NO5	6.99	571.5174	-0.381	25201286  	2-hydroxy-N-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide
Cer 18:1;3O/16:0;(2OH)	C34H67NO5	5.9	569.5017	-0.488	138199787  	LASIERQJQDQHBD-XUTLUUPISA-N  
Cer 26:0;2O/20:0	C46H93NO3	17.87	707.7153	-0.355	138131378 	BWLSZCVPXQYDMM-UHFFFAOYSA-N
Chrysanthemin	C21H20O11	0.58	448.1009	0.654	44256715	RKWHWFONKJEUEF-GQUPQBGVSA-O
Di(2-nonyl) phthalate	C26H42O4	7.77	418.3081	-0.584	5651773	MZHUXOCCLPGHKA-UHFFFAOYSA-N 
Dilauryl thiodipropionate	C30H58O4S	10.06	514.4055	0.144	31250  	GHKOFFNLGXMVNJ-UHFFFAOYSA-N
Dioctyl phthalate	C24H38O4	1.61	390.2769	-0.305	8346	MQIUGAXCHLFZKX-UHFFFAOYSA-N
Ergosterol peroxide	C28H44O3	1.66	428.3288	-0.402	5351516  	VXOZCESVZIRHCJ-KGHQQZOUSA-N
Erucamide	C22H43NO	2.56	337.3346	0.503	5365371	UAUDZVJPLUQNMU-KTKRTIGZSA-N
LPC 16:0-SN2	C24H50NO7P	0.78	495.3322	-0.65	0097314 	ASWBNKHCZGQVJV-QHCPKHFHSA-N 
LPC 18:1-SN2	C26H52NO7P	0.79	521.3482	0.102	16081932	AMUFBLWGFFICM-PTGWMXDISA-N
Lupenone	C30H48O	6.16	424.3701	-0.961	92158  	GRBHNQFQFHLCHO-BHMAJAPKSA-N
N,N-dimethyldodecylamine N-oxide	C14H31NO	0.72	229.2406	-0.068	15433	SYELZBGXAIXKHU-UHFFFAOYSA-N
N-nervonoyl-D-erythro-sphinganine	C42H83NO3	16.53	649.6366	-1.046	5283576  	YUULKFVZRXQHPM-ATHUGRIKSA-N
N-octylsphingosine	C26H53NO2	6.09	411.4072	-1.113	16759361  	CSRGRGSMEUKQSD-XQAXIDAFSA-N
N-palmitoylsphingosine	C34H67NO3	8.83	537.512	-0.167	5283564	YDNKGFDKKRUKPY-TURZORIXSA-N
PC 16:0_16:0	C40H80NO8P	8.85	733.5614	-0.971	452110	KILNVBDSWZSGLL-KXQOOQHDSA-N
PC 16:0_18:3	C42H78NO8P	5.6	755.5463	0.472	138298163	XNMRFFRAJXHEBK-GEUDNWMBSA-N
PC 18:0_14:1	C40H78NO8P	6.66	731.546	-0.727	138183198  	JAYJLDJDIZHIGU-SQFISAMPSA-N 
PC 18:0_16:2	C42H80NO8P	6.75	757.5611	-1.409	138309767 	YXPODHSGZFOKCJ-OHNCOSGTSA-N 
PC 18:0_18:2	C44H84NO8P	9.91	785.5925	-1.283	138241186	PZANWOBHYGUINP-XPGOGURHSA-N 
PC 18:1_18:3	C44H80NO8P	5.69	781.561	-1.455	53478727 	DPEYXLDDNACOGV-ANVMUZGGSA-N
PC 18:2_16:4	C42H72NO8P	1.58	749.4989	-0.852	138173366 	HWQKUQXPFGSZDW-IVEPRVLKSA-N
PC 18:2_18:3	C44H78NO8P	4.02	779.5455	-1.279	138301656	XYFKJQFHIJRBSL-OFWSBFIXSA-N
PC 18:3_18:3	C44H76NO8P	2.54	777.5299	-1.183	138269404  	UCCKRFLYRWRGGT-RSLAUBRISA-N 
PC 20:0_14:1165245428	C42H82NO8P	9.17	759.577	-1.042	165245428 	XGWGPVSNKQXRB-SQFISAMPSA-N
PE 15:0_17:1	C37H72NO8P	8.13	689.4993	-0.365	138164629  	GVNQNKPKRJLYHA-ICFOKQHNSA-N
PE 16:0_16:1	C37H72NO8P	7.23	689.499	-0.779	71627298  	CZOSTDZGCCEZTJ-PEZBUJJGSA-N  
PE 17:1_17:1	C39H74NO8P	7.36	715.5145	-0.958	138229286 	OOKVUXFXZHUJGT-IQRFGFHNSA-N
Pelargonidin 3-O-glucoside	C21H20O10	0.56	432.1064	1.682	443648	ABVCUBUIXWJYSE-GQUPQBGVSA-O
Pelargonin	C27H30O15	0.57	594.1583	-0.229	44256620	SLCKJKWFULXZBD-ZOTFFYTFSA-O
Pheophorbide A	C35H36N4O5	0.83	592.2693	1.163	253193	NSFSLUUZQIAOOX-QEWKCGBTSA-N
Sphingosine	C18H37NO2	0.93	299.2823	-0.49	5280335	WWUZIQQURGPMPG-KRWOKUGFSA-N
Stearic acid ethyl ester	C20H40O2	5.78	312.3028	-0.16	 8122  	MVLVMROFTAUDAG-UHFFFAOYSA-N  
Tetrahydrodicranenone B	C18H28O3	0.71	292.2037	-0.275	10424442  	RHVWQVSLVMXMBR-CLTKARDFSA-N
TG 16:0_18:3_18:3	C55H94O6	17.73	850.7024	-3.066	25240837 	GLKWVCJIQVMKME-HTINPRBKSA-N
TG 16:3_16:3_18:3	C53H84O6	16.17	816.6252	-2.13	65221020 	HEUOJQFDCRSAQQ-BLMRINQCSA-N 
TG 18:0_18:3_18:3	C57H98O6	18.05	878.7331	-2.973	25241102 	DKDIPDJHNARQPL-KLYSNINRSA-N
TG 18:3_18:3_18:3	C57H92O6	17.09	872.687	-2.285	5462874 	UBEIMDKGOYBUKT-FLIQGJDUSA-N
Triphenylphosphine oxide	C18H15OP	0.67	278.0859	-0.49	13097  	FIQMHBFVRAXMOP-UHFFFAOYSA-N  
Vitamin K1	C31H46O2	10.07	450.3499	0.26	5280483	MBWXNTAXLNYFJB-LKUDQCMESA-N
Vitamin K1 2,3-epoxide	C31H46O3	2.91	466.3447	0.049	5280845  	KUTXFBIHPWIDJQ-LKUDQCMESA-N 
Vitexin 4-O-glucoside	C27H30O15	0.57	594.1579	-0.944	44257745	CQJPSSJEHVNDFL-JCCJKREVSA-N
Zymosterol	C27H44O	5.67	384.3391	-0.58	92746	CGSJXLIKVBJVRY-XTGBIJOFSA-N
METABOLITES_END
#END