#METABOLOMICS WORKBENCH jord001_20250201_151607 DATATRACK_ID:5587 STUDY_ID:ST003998 ANALYSIS_ID:AN006590 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        	A Thermo Vanquish was used for the analysis of the polar phase secondary
CH:CHROMATOGRAPHY_SUMMARY        	metabolites. Chromatographic separation of the liquid-phase chemical components
CH:CHROMATOGRAPHY_SUMMARY        	was achieved using a C18 column (2.1 × 100 mm, 1.7µm) Waters, Milford, MA,
CH:CHROMATOGRAPHY_SUMMARY        	USA, coupled to a UPLC BEH C18 column (2.1 × 10mm, 1.7µm) with a flow rate of
CH:CHROMATOGRAPHY_SUMMARY        	0.4 mL/min. Two solutions were used for the mobile phase, namely Solution A
CH:CHROMATOGRAPHY_SUMMARY        	(100% water; 0.1% formic acid) and Solution B (100% acetonitrile; 0.1% formic
CH:CHROMATOGRAPHY_SUMMARY        	acid).
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                     	100% water; 0.1% formic acid
CH:SOLVENT_B                     	100% acetonitrile; 0.1% formic acid
CH:FLOW_GRADIENT                 	The gradient was linearly changed as follows: 0−2 min, 100% B; 2−9 min from
CH:FLOW_GRADIENT                 	100% B to 85% B; 9−14 min from 85% B to 50% B; 14−17 min from 50% B to
CH:FLOW_GRADIENT                 	100%B, 17.1−20 min, 100% B for column re-equilibration.
CH:FLOW_RATE                     	0.4 mL/min
CH:COLUMN_TEMPERATURE            	35°C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Thermo Orbitrap ID-X Tribrid
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	POSITIVE
MS:MS_COMMENTS                   	The Thermo Orbitrap ID-X tribrid was used. This instrument was operated using
MS:MS_COMMENTS                   	following parameters were: sheath gas at 50 arb, auxiliary gas at 10 arb, spray
MS:MS_COMMENTS                   	voltage at +3.5 kV in positive mode and 2.5kV, capillary temperature at 300
MS:MS_COMMENTS                   	◦C, auxiliary gas heater temperature at 350°C, s-lens RF level at 60%. Full
MS:MS_COMMENTS                   	scan parameters: m/z range from 50 to 500; mass resolution, 60,000; AGC target,
MS:MS_COMMENTS                   	3e6; maximum IT, 100ms. DDA parameters: m/z range from 50 to 500, TopN, 3
MS:MS_COMMENTS                   	(fragments the 3 ions with top intensities from the previous full scan
MS:MS_COMMENTS                   	spectrum); intensity threshold to trigger MS/MS acquisition, 2e4; dynamic
MS:MS_COMMENTS                   	exclusion, 6 s; combined MSMS CE at 10, 30, 40, 70, 90 eV, mass resolution,
MS:MS_COMMENTS                   	30,000; AGC target, 1e5; maximum IT, 50ms; m/z isolation window within 1.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	AUC
MS_METABOLITE_DATA_START
Samples	A1	A2	A3	A4	A5	E1	E2	E3	E4	E5	C1	C2	C3	C4	C5	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: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: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: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
(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate	6060780.397	6422154.377	5581795.878	5979500.788	5735007.062	7311.230639	38773126.67	13746454.97	68493538.15	16713095.38	186061625.5	221702296.5	85419668.31	243937624.6	218167753.9	129787225.4	219377386.1	211227194.3	186052237.5	287015868.2	377182344.4	340417542.9	316349660.1	370620961.6	347664083.2
1-Methyladenine	2548251.117	2443327.395	1828914.138	2166179.331	2101292.497	101121.8908	846462.1022	445070.8612	6061938.413	21931250.29	266677895	295815034.3	331904975.2	324423825	319065510.2	356360824.6	478342299.7	91307922.34	425606224.8	445696485.7	484194770.7	458599774.9	419613044.3	486892808.5	453629300.6
1-Tetradecylamine	30573540.61	41605857.39	18477282.54	24069072.39	44204958.03	13989344.02	8002.082931	6304.197096	28669.99568	206717.5954	4898888.524	4691227.522	4888863.516	5076318.278	4822367.164	2985335.249	2825908.198	3432404.657	2702491.086	3222450.842	3325268.725	3276210.965	3943736.664	3237971.341	2828924.793
2,3,4,9-Tetrahydro-1H-β-carboline-3-carboxylic acid	610483.5494	516086.9937	360638.6794	879395.344	462451.7897	29471.21886	2174147.378	1976859.393	5325774.104	11931307.29	10439683.9	7196440.876	7276545.869	20877102.9	8820351.984	2377071.5	2832721.077	2694185.216	2976809.666	3917965.629	213362.8372	152377.5019	479365.9736	484682.3013	296292.1545
2-Amino-1,3,4-octadecanetriol	4080833.773	4423520.316	3045798.812	2902560.891	4309598.861	150063.9826	43789.44873	47531.21236	51174.01986	45047.30392	5532593.53	4302575.313	4074060.562	18001419.24	4981619.28	1741210.317	2053168.157	2308850.643	2698205.151	1471603.518	110988.9443	119808.0486	100799.0495	108391.6193	124086.3332
2-Hydroxycinnamic acid	5815456.516	5204402.151	4377942.093	4665013.864	4615803.47	11342.65602	21164027.63	26872468.09	318183391.7	21079555.31	1114000317	1263079196	1219646959	1344780449	1230518199	826817769.4	1266956803	984740032.2	1179626474	1200812282	16104866.22	8440885.858	14950451.01	8219268.618	8804163.253
2'-O-Methyladenosine	1762909.922	1058925.119	1070248.527	1183440.377	1172281.909	3257865.021	4462.565444	4346.168042	9258.521229	4930.953265	294620.2137	298004.4924	350743.3282	479600.2905	347911.8265	165073.5831	356939.6374	227667.3297	270705.0458	282250.1657	46590.99517	45255.72947	44062.87759	46124.88131	50157.14323
4-(4-hydroxy-2,2,6-trimethyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene)but-3-en-2-one	9047566.258	7597394.648	6119150.588	7138510.02	7468122.044	7493.336762	2594623.557	3096207.243	2425040.063	650139.7424	35996176.07	43976581.94	42095044.2	40427629.23	36872420.44	29377740.69	45066721.17	30412702.87	39201434.26	40417144.64	23367905.69	21988262.11	19191401.57	21658165.3	22650671.25
4H-1-Benzopyran-4-one	5544894.246	4961966.07	3712404.101	4552022.604	4055251.448	5832.656361	58008.08668	30986.99253	473487.5832	862313.0625	32550081.13	39025856.27	36781541.37	37599990.6	36954969.56	26196094	39093532.5	30842669.7	36277637.51	40337203.07	32097541.93	33580717.12	30763290.19	44529031.16	44243526.44
4-Indolecarbaldehyde	3206630.907	4119384.621	4298545.596	4017464.08	4139050.943	8261734.831	33425.09908	31314.33228	227317.9073	90195.33581	14115973.91	15873365.34	18769136.19	18720236.18	17321333.83	10239897.8	22471131.48	9485076.913	16921046.24	20223081.67	24800907.71	24992005.01	21107953.96	30342808.62	26040213.38
4-Pyridoxic acid	1111444.562	1922868.289	1399697.816	1645553.863	1729435.68	21321.56992	207024.3009	375366.2121	1324299.909	33335505.59	97553720.59	95496482.21	96720263.16	134619008.7	106915896.7	91805113.45	106780734.8	91488751.78	88998141.99	89986094.46	57565147.37	50042496.51	49177849.29	61482354.18	43508877.7
5-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one	2906570.858	1983516.683	1626022.883	1926218.52	1656434.519	15618.67317	219750.5266	110929.3382	695994.4312	12544.86885	420798.3162	468926.2647	494772.1821	567578.8334	451197.6241	396021.6607	621999.9874	386575.9584	500252.2604	608592.7336	561403.6048	463508.1384	413949.2199	484561.0979	596595.0705
7-methoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one	188221.2071	348231.1566	186929.0763	228245.8221	264928.9253	39721.45066	6866937.128	5227400.318	6139629.432	5752679.027	4228171.092	4573604.195	3509310.974	5261813.457	5234080.064	3916736.483	4524916.282	3760898.987	4855520.544	5666121.884	882592.8512	954178.0185	865888.1453	933507.1603	1168105.012
8-{3-Oxo-2-[(2E)-2-penten-1-yl]-1-cyclopenten-1-yl}octanoic acid	1067741.819	706485.5191	631856.2914	533258.8907	862391.6976	1329973.784	26483.38748	16200.24593	237404.3841	111390.77	3771557.937	4952656.281	4439633.951	5330106.02	4579214.334	2946384.82	5255080.275	3324254.603	4516466.777	5070182.633	4886165.95	4619042.62	4034467.356	4949711.62	4664207.117
9-Oxo-10(E),12(E)-octadecadienoic acid	5525122.949	3761570.313	2800546.781	2421302.394	4632597.385	21672595.65	59617.56974	49359.33803	1279121.3	317823.0592	10415357.54	13189301.36	11161659.18	13067585.05	11375874.71	9112113.103	14082548.85	9566347.678	12533562.68	13675659.77	13935176.05	14113442.21	12116132.16	14022722.04	13924534.17
9S,13R-12-Oxophytodienoic acid	1694782.306	226498273.3	154971758.3	119312536.1	225965752.9	17161735.13	465541.3169	441223.4134	203898.4972	561685.4227	4616966.913	5616833.258	4304512.397	4834702.866	5879839.162	1177981.934	4651990.607	2469516.644	6489043.395	3892707.571	1242567.818	1759203.366	1106236.562	1126286.352	887509.3534
Acetylarginine	571988.884	549522.477	364103.8633	512625.1185	435753.5964	6482.039193	152192.3274	66116.30532	9991436.787	33866115.58	96253335.72	82386058.62	118030299.4	238452695.3	115220298.5	74363667.97	139841266.4	63093981.63	72419682.22	72234299.31	104343088.8	109672074.9	92718666.84	98922188.8	104517446.1
Adenosine	28656907.24	20260580.19	37719296.97	26796621.49	21674784.22	1653550.312	34941.76029	30424.88736	41589.70965	118546.569	3708561.888	4087130.857	4652694.545	4259736.936	4373844.718	4417794.33	8051293.258	4736734.193	6822873.659	7321360.82	7985040.458	7368051.486	7119652.046	7160440.339	7640651.652
Adenosine 3'5'-cyclic monophosphate	7199399.37	6799311.657	9518371.323	6529952.355	5379938.699	46019.5148	11014837.45	11191304.98	8062336.693	9601760.676	3719707.238	4736610.695	3916077.579	4671386.476	4030120.53	3455717.804	4457448.209	3275513.756	4598504.638	3596552.4	392330.4229	866519.3343	427185.342	351534.7526	431499.3242
Apigetrin	1471256830	1381251171	1262524758	1337767935	1339086193	12420164.99	10298.74764	11834.07245	130831.2265	221122.0098	1673226.411	1050515.622	746468.9809	7534563.269	2247930.246	534408.113	1690480.545	203788.1686	726852.5118	494702.7805	634324.4674	427742.7087	481116.8322	613890.9728	599722.107
D-(+)-Proline	27360834.85	26918129.55	22172342.36	27097489.31	21977585.92	3757883.873	221337.5774	390805.1875	487500.763	480550.4687	2216249.36	311279.9484	1176036.324	274298.5761	972776.9835	903434.0297	44414376.4	7301839.567	7468768.282	35145737.91	532257838.9	517886277.7	333906867	404067057.3	405569694.3
D-(+)-Pyroglutamic Acid	14929858.27	14035868.03	10960972.51	12885686.1	11918828.88	32752.8909	12796.87443	9510.072501	86030.54293	11544.65327	1773670.575	2308872.775	998058.1152	2793854.528	1045172.947	1156248.63	2146885.506	1378056.5	1776002.326	1890551.189	66708.91053	61882.56091	56394.91963	66732.42524	63702.41609
D-Carnitine	7913477.33	7737140.672	7809560.667	7130792.264	7150435.93	413072.7102	20293.36969	53071.81333	64057.2668	69720.9461	1439417.542	2109215.229	2164896.407	2257322.736	1945146.039	1226289.781	3872966.453	1685997.864	3060442.41	3659442.888	5823342.703	5366490.476	4498136.367	5530422.304	5158631.775
Desthiobiotin	473148.8511	464351.2272	328437.8197	368013.1535	339985.1011	115331.4553	9460.952939	7544.756735	261192.0887	51454.95332	2201152.306	2666071.969	3203505.447	1905040.907	2867661.74	2506566.465	3071622.92	2542747.219	3000546.732	2888336.073	23783.0636	22667.92351	29551.34963	23568.96456	22081.53018
Diosmetin	4334994.734	5250807.711	2767823.772	3511989.088	5054205.333	3572043.499	1482400.053	158723.9364	1822047.177	1405521.411	9589140.138	14969112.75	12315468.12	18917278.39	17897535.84	12478906.01	22065907.76	13484205.92	15783341.72	13444210.1	144745.2496	161797.4812	249158.4469	199853.3308	147816.9218
Galangin	7953765.58	6226956.556	5745499.72	6384678.962	5706177.49	420236.462	62229.52301	23903.3244	570041.5203	352258.9054	10102078.04	12218441.91	12622391.82	19459739.83	14331997.06	6526082.758	17145580.28	8629621.51	12676568.39	11365081.91	41154053.5	44470168.85	35661869.54	40142005.29	47287074.86
Inosine	4892826.786	4435575.63	5725238.332	4741152.629	3230188.054	11623.93049	7325.974056	6426.468064	34629.22768	40932.17077	732426.276	764912.9754	848008.0235	763429.5785	813184.4569	678053.6664	658357.7955	704558.1798	450477.2229	526824.9064	821593.4121	637857.1131	915911.4461	571096.0356	707108.8432
Isonaringin	3176548.772	2455611.851	2328422.062	2701199.76	2520901.267	9798.565475	352562.593	340921.1542	2668050.553	2932329.583	3113237.143	3462144.59	2729969.787	3483041.629	3373989.523	2175584.425	2212955.514	2611847.894	2277708.049	2555293.719	669408.2547	803256.0393	943361.0471	779364.6153	680738.6667
Kaempferol	2039775.186	1904274.413	1355922.284	1872655.159	1967131.526	52354.92837	72545.79069	71958.09835	305386.9845	122428.2394	2205233.631	5374054.396	4838206.662	4100090.865	4814901.529	3271660.369	7275672.094	2769995.311	4919360.011	2657164.859	105268264.5	105754760.5	95725462.94	104787896.6	109025984.7
Kuromanin	762044.4097	1531128.945	800941.1579	1920126.364	780374.3722	255378.3889	25370.11618	31302.62165	491414.5553	2023822.837	16657234.97	21348749.44	21678890.53	19953026.9	19926430.86	18109857.78	26169885.86	22379385.33	19890709.66	26666127.46	19325415.09	21331960.51	18211711.07	19363695.02	16663287.72
Kynurenic acid	13704346.15	12613425.84	9664470.543	11208559.49	9309441.305	53408.95297	8633.777633	13762.20118	49224.63707	441164.7755	3307764.719	2412759.083	2237549.99	2445456.376	2137574.902	862625.4117	2418532.387	877395.3112	2394774.222	1543727.588	22260989.14	17376471.63	16994884	23829173.14	21128185.32
L(+)-Ornithine	78364.08697	58451.44532	74616.13892	54287.96565	71906.79022	6697.709245	72879.8485	58766.98845	1607760.186	1555387.388	31902768.86	34615662.48	37306384.09	36574762.37	36051659.52	28340802.14	34060698.05	27358645.48	36056875.74	32401024.14	41107139.29	38732296.17	38772881.17	41235116.61	38789961.31
Leucine	2175936.179	2446322.075	1839796.836	1963376.878	2520130.639	572203.0544	645877.2547	560143.1953	3909310.332	3118873.9	135378891.3	171621050.9	182338611.7	209379384	167246449.9	116084350.1	212482028.1	111847488	164548330.6	182290427.6	372077124.5	370231059.2	342196560	385633849	377651665.8
Leucylproline	4703155.281	2905331.303	1999780.023	4270048.169	2511853.256	87789.71091	18857.74491	13112.85738	145991.0663	112194.9979	9458278.56	11557213.92	13712245.47	13600452.81	12938339.99	9959588.688	451930.5602	7624376.16	11073586.92	12058920.41	28526049.28	27213918.92	25724958.05	31304313.09	28371381.35
L-Glutamic acid	604528.8861	395669.676	400763.6855	362169.4575	464318.3453	71933.42304	7473.216702	7511.294631	39493.05677	8561.209155	2345624.444	2975239.725	3104406.546	3668645.395	3173067.173	2190206.953	3813088.723	2324151.049	3200112.224	2879625.214	87663.03846	56515.91027	51573.10859	148679.7479	59441.02471
L-Phenylalanine	103629842.3	98520802.4	75516280.55	95121265.45	76117598.01	653546.3024	116905.5322	87564.29762	23026.22108	8908.393578	775729.8746	799901.6339	538166.3581	815696.2121	709141.5586	455551.1845	809658.2239	661698.0839	654714.7728	834754.3678	1425111.201	1449872.623	1638012.09	1494662.685	1626316.36
L-Tyrosine	5402610.904	5728645.649	4057848.62	6287683.974	3809961.448	6822.160874	215588.2086	181474.6749	2428874.757	1444127.12	36975743.19	46485156.13	41929963.6	49990002.04	44945408.12	29657043.99	49236640.66	34478984.55	42303184.53	47317026.76	44330565.45	43350034.63	36108634.63	43243955.19	41587388.6
Luteolin-3',7-Diglucoside	3055249.071	2975145.986	2085422.121	2982866.989	2012831.049	5784.91409	564208.552	328735.4057	466152.6663	374854.2607	1009289.617	1102658.251	575339.5877	1242822.363	1001304.09	581816.3887	1337644.493	641446.0783	880699.3616	1199421.761	213870.1703	192926.2159	260700.2276	289573.7842	306559.6604
N1-(2-oxopropyl)-2-phenylacetamide	773978.8821	765327.9327	806035.0521	657085.5363	858020.7933	85492.56315	29711.22133	37037.89713	769967.3562	3770387.713	49267052.37	54296259.4	47194613.51	54970182.38	52379344.27	39572528.85	42457428.82	42392940.31	43222121.6	41952202.37	40060637.84	40538971.73	43444998.29	42432069.32	39308756.79
Nicotinic acid	44908502.28	39625110.97	31291575.93	36756825.02	34306962.86	171309.1518	59880.06165	46605.14716	96899.8058	179981.9921	1628351.976	2298517.525	2063981.351	2103394.466	2144838.569	1985575.614	2897160.715	1924109.849	2930687.911	2968302.52	5844325.554	5774152.049	5088579.069	6104994.763	5434536.553
Nobiletin	1049535.262	925478.3395	486610.1707	765888.5916	905715.8033	333867.2847	3469734.493	4764091.026	1727163.477	2433518.663	2358401.314	2629002.829	2312903.628	2849161.722	2679082.511	1054818.18	1832649.668	1528551.854	1842503.156	1682683.703	1547458.811	1191823.576	1348639.519	1101691.551	1805029.442
Quinoline	2190398.221	1984182.677	1640749.506	1897257.054	2059731.925	1666252.745	79598.2765	107030.9424	1465433.843	55990.57115	8822314.132	10493624.88	10012901.9	10534981.03	9763603.258	5642029.042	11165451.42	7513949.456	9485414.9	9794425.888	43847.77025	40650.51407	44080.40284	40258.81899	43082.71573
Scutellarein 7-methyl ether 6-glucoside	11215423.92	11601523.24	9304579.475	11107776.61	11072967.27	78349.07476	899914.1781	908925.8161	697904.147	712705.1291	1089985.318	1311884.634	711864.2043	1180701.159	968500.9753	952251.765	859076.3674	883837.8485	660426.8997	1242418.225	438021.8772	328432.7323	469698.402	452125.7983	298363.9766
Sorbic acid	1430545.167	1342857.14	667500.5069	1166596.751	1463954.26	55052772.61	191290.728	162144.8879	182651.2037	167740.8794	362867.2807	315518.189	207209.0392	509344.2453	304140.5097	185549.3839	554896.9658	227901.581	362446.8712	379444.2853	69411.65527	73214.54855	68861.4681	96462.32391	95609.87705
Tangeritin	393337.1792	315125.922	228543.9555	300480.356	314161.5045	175257.1897	6942.500023	5465.518288	20019.39211	7112.362786	1521365.805	3730166.794	4853334.124	2093736.771	2170560.128	7022329.351	13804686.77	8281799.562	18718800.32	20578759.28	3262027.048	3495343.571	2524216.235	2248153.871	1040797.63
Tetramethylpyrazine	2645170.202	1719739.564	1331540.606	2625937.584	1082493.44	6901.187792	574583.671	1073710.328	5496823.577	3425946.792	245129271.5	289016179.9	297453076.2	295257653.8	282261787.2	187184501.7	316980970.1	188516637.5	269011054	267892477	307775386.5	305369710.7	285875275.3	353581235.1	313670374.2
trans-3-Indoleacrylic acid	210429352.1	214823653.3	155285328.9	210875279.2	144338886.4	837990.6058	24342.28025	26581.64854	2679242.944	26493.07891	104121.1531	118327.1013	129837.3486	129275.4808	116695.5688	110314.6191	137820.5968	113693.296	161961.5121	160953.5529	168646.9729	185659.1745	158720.4911	158312.6208	160926.7215
trans-Zeatin	20345992.27	12154939.46	16643249.99	17945194.26	12483815.11	32474.12541	281003.3603	95123.77749	488539.6443	358200.5841	2844648.434	6195810.861	5553109.019	3912836.466	4455234.13	3862724.89	7476222.45	3287042.531	7340913.587	4541431.844	67535.00267	67216.03485	57480.51203	67316.0078	66344.58474
Trifolin	2687039.77	2329699.69	1494962.435	2281899.372	1522048.357	126933.9678	33535.04922	22089.22479	408819.744	88239.97288	9809754.062	12321037.62	11715229.78	11407721	10423088.91	8113879.186	10678914.46	7611588.429	10503427.71	11592543.76	6049607.549	5211009.043	4574794.844	4614233.059	5823696.149
Valylproline	8994652.842	8367923.068	6577504.023	8581171.856	7335890.924	10033.49209	19420.46151	7149.155068	117124.2531	75256.53503	1678655.671	2233240.844	2160752.778	3962034.213	2515172.053	1481307.281	3159296.394	1465665.348	2068363.458	1986219.201	14336982.35	14728723.03	11827378.68	14235738.62	14542756.19
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	Formula	Annot. DeltaMass [ppm]	Calc. MW	RT [min]	Pubchem CID	INCHI_KEY
(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate	C22 H30 O14	0.96	518.1641	4.299	56776292  	XMBZZLUIFFOAHR-HWKANZROSA-N 
1-Methyladenine	C6 H7 N5	0.27	149.0702	0.79	135398646	SATCOUWSAZBIJO-UHFFFAOYSA-N
1-Tetradecylamine	C18 H28 O3	0.33	292.2039	6.389	16217  	PLZVEHJLHYMBBY-UHFFFAOYSA-N 
2,3,4,9-Tetrahydro-1H-β-carboline-3-carboxylic acid	C12 H12 N2 O2	0.11	216.0899	4.211	98285	FSNCEEGOMTYXKY-UHFFFAOYSA-N
2-Amino-1,3,4-octadecanetriol	C16 H12 O6	-0.57	300.0632	6.699	248575  	AERBNCYCJBRYDG-UHFFFAOYSA-N  
2-Hydroxycinnamic acid	C9 H8 O3	0.42	164.0474	4.173	637540	PMOWTIHVNWZYFI-AATRIKPKSA-N
2'-O-Methyladenosine	C11 H15 N5 O4	0.51	281.1126	1.457	102213	FPUGCISOLXNPPC-IOSLPCCCSA-N
4-(4-hydroxy-2,2,6-trimethyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene)but-3-en-2-one	C19 H30 O8	0.54	386.1943	4.666	10135731	BFLLXOGGWRRMBS-WRQFPXLNSA-N
4H-1-Benzopyran-4-one	C27 H30 O16	0.55	610.1537	4.433	10286  	OTAFHZMPRISVEM-UHFFFAOYSA-N 
4-Indolecarbaldehyde	C9 H7 N O	0.3	145.0528	3.449	333703	JFDDFGLNZWNJTK-UHFFFAOYSA-N
4-Pyridoxic acid	C8 H9 N O4	0.72	183.0533	1.798	6723	HXACOUQIXZGNBF-UHFFFAOYSA-N
5-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one	C16 H18 O8	0.44	338.1003	4.35	196468	DXBGTODWNFZHCD-LMXXTMHSSA-N
7-methoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one	C18 H39 N O3	0.44	317.2931	6.786	3084335	WBAVLTNIRYDCPM-YMILTQATSA-N
8-{3-Oxo-2-[(2E)-2-penten-1-yl]-1-cyclopenten-1-yl}octanoic acid	C20 H20 O7	0.88	372.1212	7.501	71348099	PMTMAFAPLCGXGK-CVEARBPZSA-N
9-Oxo-10(E),12(E)-octadecadienoic acid	C18 H28 O3	1.16	292.2042	7.925	9839084	LUZSWWYKKLTDHU-ZJHFMPGASA-N
9S,13R-12-Oxophytodienoic acid	C6 H5 N O3	0.31	139.027	6.058	14037063 	PMTMAFAPLCGXGK-TTXFDSJOSA-N 
Acetylarginine	C8 H16 N4 O3	0.25	216.1223	0.826	67427	SNEIUMQYRCDYCH-LURJTMIESA-N
Adenosine	C10 H13 N5 O4	0.56	267.0969	0.943	60961	OIRDTQYFTABQOQ-KQYNXXCUSA-N
Adenosine 3'5'-cyclic monophosphate	C10 H12 N5 O6 P	0.52	329.0527	2.405	6076	IVOMOUWHDPKRLL-KQYNXXCUSA-N
Apigetrin	C21 H20 O10	0.49	432.1059	5.442	5280704 	KMOUJOKENFFTPU-QNDFHXLGSA-N  
D-(+)-Proline	C5 H9 N O2	0.64	115.0634	4.643	8988	ONIBWKKTOPOVIA-SCSAIBSYSA-N
D-(+)-Pyroglutamic Acid	C5 H7 N O3	0.75	129.0427	1.267	439685	ODHCTXKNWHHXJC-GSVOUGTGSA-N
D-Carnitine	C11 H12 N2 O2	-0.37	204.0898	3.511	9060	QIVBCDIJIAJPQS-SECBINFHSA-N
Desthiobiotin	C7 H15 N O3	0.16	161.1052	0.788	2724480	PHIQHXFUZVPYII-LURJTMIESA-N
Diosmetin	C10 H18 N2 O3	0.11	214.1318	5.018	445027	AUTOLBMXDDTRRT-JGVFFNPUSA-N
Galangin	C9 H7 N O	0.4	145.0528	5.645	12736	TVIDDXQYHWJXFK-UHFFFAOYSA-N
Inosine	C16 H12 O6	0.59	300.0636	6.611	5281628	IHFBPDAQLQOCBX-UHFFFAOYSA-N
Isonaringin	C6 H8 O7	0.19	192.027	1.785	5318532	ODBLHEXUDAPZAU-ZAFYKAAXSA-N
Kaempferol	C8 H6 O4	0.07	166.0266	5.392	8496 	QQVIHTHCMHWDBS-UHFFFAOYSA-N  
Kuromanin	C15 H10 O6	0.51	286.0479	5.408	5280863	IYRMWMYZSQPJKC-UHFFFAOYSA-N
Kynurenic acid	C21 H20 O11	0.35	448.1007	5.204	441667  	RKWHWFONKJEUEF-GQUPQBGVSA-O
L(+)-Ornithine	C5 H12 N2 O2	0.59	132.09	0.862	6262	AHLPHDHHMVZTML-BYPYZUCNSA-N
Leucine	C6 H13 N O2	0.65	131.0947	0.78	6106	ROHFNLRQFUQHCH-YFKPBYRVSA-N
Leucylproline	C11 H20 N2 O3	0.15	228.1474	3.325	80817	VTJUNIYRYIAIHF-IUCAKERBSA-N
L-Glutamic acid	C5 H9 N O4	0.35	147.0532	0.947	33032	WHUUTDBJXJRKMK-VKHMYHEASA-N
L-Phenylalanine	C9 H11 N O2	0.42	165.0791	1.766	6140	COLNVLDHVKWLRT-QMMMGPOBSA-N
L-Tyrosine	C9 H11 N O3	0.28	181.0739	1.237	6057	OUYCCCASQSFEME-QMMMGPOBSA-N
Luteolin-3',7-Diglucoside	C27 H30 O16	0.38	610.1536	4.853	14769205  	BISZYPSIZGKOFA-UHFFFAOYSA-N
N1-(2-oxopropyl)-2-phenylacetamide	C15 H10 O5	1.83	270.0533	5.814	2801284 	QZUOKPUQPUDFNS-UHFFFAOYSA-N
Nicotinic acid	C6 H5 N O2	0.57	123.0321	1.241	938	PVNIIMVLHYAWGP-UHFFFAOYSA-N
Nobiletin	C6 H8 O2	0.83	112.0525	7.171	72344	MRIAQLRQZPPODS-UHFFFAOYSA-N
Quinoline	C9 H7 N	0.7	129.0579	5.001	7047	SMWDFEZZVXVKRB-UHFFFAOYSA-N
Scutellarein 7-methyl ether 6-glucoside	C22 H22 O11	0.83	462.1166	5.502	44258459  	JSUJHPSAVAWXEN-CIIGYETHSA-N 
Sorbic acid	C16 H18 O9	0.09	354.0951	6.796	643460	WSWCOQWTEOXDQX-MQQKCMAXSA-N
Tangeritin	C21 H22 O8	0.66	402.1317	7.183	68077  	ULSUXBXHSYSGDT-UHFFFAOYSA-N  
Tetramethylpyrazine	C8 H12 N2	0.53	136.1001	4.165	14296	FINHMKGKINIASC-UHFFFAOYSA-N
trans-3-Indoleacrylic acid	C11 H9 N O2	0.08	187.0633	3.444	5375048	PLVPPLCLBIEYEA-AATRIKPKSA-N
trans-Zeatin	C10 H13 N5 O	0.21	219.1121	1.751	449093	UZKQTCBAMSWPJD-FARCUNLSSA-N
Trifolin	C10 H7 N O3	0.28	189.0427	5.535	44258737	JPUKWEQWGBDDQB-DTGCRPNFSA-N
Valylproline	C10 H18 N2 O3	0.39	214.1318	5.243	9837272	GIAZPLMMQOERPN-YUMQZZPRSA-N
METABOLITES_END
#END