#METABOLOMICS WORKBENCH M_Sasaki_20230421_000842 DATATRACK_ID:3879 STUDY_ID:ST002584 ANALYSIS_ID:AN004255 PROJECT_ID:PR001664 VERSION 1 CREATED_ON April 26, 2023, 11:57 am #PROJECT PR:PROJECT_TITLE Metabolomics analysis of ALDH1L1-expressing HuH-7 cell line. PR:PROJECT_SUMMARY Quantitative metabolomics study of the effect of the folate metabolizing enzyme PR:PROJECT_SUMMARY ALDH1L1 on the HuH-7 cell line. PR:INSTITUTE Tohoku Medical and Pharmaceutical University PR:LAST_NAME Sasaki PR:FIRST_NAME Masato PR:ADDRESS 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan PR:EMAIL msasaki@tohoku-mpu.ac.jp PR:PHONE +81-22-727-0132 #STUDY ST:STUDY_TITLE Metabolomics analysis of ALDH1L1-expressing HuH7 cell lines. ST:STUDY_SUMMARY One-carbon metabolism is utilized for the de novo synthesis of purines. Given ST:STUDY_SUMMARY that tumor cells require large amounts of nucleotides, they are highly dependent ST:STUDY_SUMMARY on one-carbon metabolism. Among the one-carbon-metabolizing enzymes, the ST:STUDY_SUMMARY aldehyde dehydrogenase 1 family member L1 (ALDH1L1), which catalyzes ST:STUDY_SUMMARY 10-formyltetrahydrofolate to trahydrofolate, is considered a tumor suppressor ST:STUDY_SUMMARY gene, as its expression is reported to be attenuated or diminished in ST:STUDY_SUMMARY hepatocellular carcinoma. To clarify the effect of ALDH1L1 expression, we ST:STUDY_SUMMARY generated control and ALDH1L1-expressing HuH-7 (H7-1L1) cells, and measured the ST:STUDY_SUMMARY amounts of intracellular metabolites in both control and ALDH1L1-expressing by ST:STUDY_SUMMARY CE-TOFMS analysis. ST:INSTITUTE Tohoku Medical and Pharmaceutical University ST:LAST_NAME Sasaki ST:FIRST_NAME Masato ST:ADDRESS 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan ST:EMAIL msasaki@tohoku-mpu.ac.jp ST:PHONE +81-22-727-0132 #SUBJECT SU:SUBJECT_TYPE Cultured cells SU:SUBJECT_SPECIES Homo sapiens SU:TAXONOMY_ID 9606 #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 L1-1 L1-1 Transgene:ALDH1L1 RAW_FILE_NAME=L1-1 SUBJECT_SAMPLE_FACTORS L1-2 L1-2 Transgene:ALDH1L1 RAW_FILE_NAME=L1-2 SUBJECT_SAMPLE_FACTORS L1-3 L1-3 Transgene:ALDH1L1 RAW_FILE_NAME=L1-3 SUBJECT_SAMPLE_FACTORS C-1 C-1 Transgene:empty RAW_FILE_NAME=C-1 SUBJECT_SAMPLE_FACTORS C-2 C-2 Transgene:empty RAW_FILE_NAME=C-2 SUBJECT_SAMPLE_FACTORS C-3 C-3 Transgene:empty RAW_FILE_NAME=C-3 #COLLECTION CO:COLLECTION_SUMMARY ALDH1L1-expressing cells or control (empty vector) cells were cultured in DMEM CO:COLLECTION_SUMMARY medium containing 5% fetal bovine serum and metabolites were collected during CO:COLLECTION_SUMMARY growing phase. CO:SAMPLE_TYPE HuH-7 cells #TREATMENT TR:TREATMENT_SUMMARY No treatment in this study. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Cells were washed with 5%(w/w) mannitol solution, and then extracted with SP:SAMPLEPREP_SUMMARY methanol. Extracts were filtered through a 5-kDa cut-off filter SP:SAMPLEPREP_SUMMARY (Ultrafree-MC-PLHCC, Human Metabolome Technologies) at 9,100 × g for 2 h at SP:SAMPLEPREP_SUMMARY 4 °C, dried in a centrifugal evaporator at 1,500 rpm at 1,000 Pa, and SP:SAMPLEPREP_SUMMARY resuspended in 50 μl of ultrapure water before metabolome analysis. #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY CE-TOFMS (ESI positive) CH:CHROMATOGRAPHY_TYPE CE CH:INSTRUMENT_NAME Agilent CE CH:COLUMN_NAME Agilent Fused silica capillary (80cm x 50um) CH:SOLVENT_A 1 M formic acid CH:SOLVENT_B - CH:FLOW_GRADIENT - CH:FLOW_RATE +30 kV CH:COLUMN_TEMPERATURE 20 #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME Agilent CE-TOFMS MS:INSTRUMENT_TYPE Other MS:MS_TYPE ESI MS:ION_MODE POSITIVE MS:MS_COMMENTS The spectrometer was scanned from m/z 50 to 1,000. Peaks were extracted using MS:MS_COMMENTS automatic integration software MasterHands (ver.2.16.0.15 Keio University). MS:MS_COMMENTS Signal peaks corresponding to isotopomers, adduct ions, and other product ions MS:MS_COMMENTS of known metabolites were excluded, and remaining peaks were annotated with MS:MS_COMMENTS putative metabolites from the HMT metabolite database based on their migration MS:MS_COMMENTS time and m/z values. Peak areas were normalized to internal standards and sample MS:MS_COMMENTS amounts. #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS relative area MS_METABOLITE_DATA_START Samples L1-1 L1-2 L1-3 C-1 C-2 C-3 Factors Transgene:ALDH1L1 Transgene:ALDH1L1 Transgene:ALDH1L1 Transgene:empty Transgene:empty Transgene:empty Pyruvic acid 9.1E-02 1.2E-01 1.2E-01 9.2E-02 1.1E-01 1.4E-01 Isobutyric acid / Butyric acid 2.7E-03 1.8E-03 2.0E-03 2.1E-03 1.8E-03 2.0E-03 Lactic acid 1.9E+00 2.0E+00 2.1E+00 1.8E+00 2.0E+00 2.3E+00 Isovaleric acid / Valeric acid 4.2E-03 3.0E-03 3.2E-03 3.1E-03 2.9E-03 2.9E-03 3-Hydroxybutyric acid 7.6E-03 7.8E-03 9.0E-03 7.4E-03 9.1E-03 9.3E-03 Glyceric acid 3.1E-03 2.9E-03 2.8E-03 2.9E-03 2.6E-03 2.6E-03 Fumaric acid 1.3E-01 1.4E-01 1.4E-01 1.3E-01 1.4E-01 1.4E-01 2-Oxoisovaleric acid 5.0E-02 4.8E-02 5.2E-02 4.4E-02 5.1E-02 5.4E-02 Hexanoic acid 1.3E-03 1.2E-03 1.3E-03 1.1E-03 1.3E-03 1.5E-03 N-Acetylglycine 7.0E-04 6.4E-04 6.2E-04 5.2E-04 5.7E-04 N.D. Succinic acid 5.8E-02 5.7E-02 6.4E-02 5.6E-02 6.2E-02 5.6E-02 2-Hydroxyvaleric acid 4.2E-03 5.3E-03 6.2E-03 4.1E-03 4.8E-03 5.8E-03 Isethionic acid N.D. 3.1E-04 N.D. 3.9E-04 N.D. N.D. 5-Oxoproline 2.1E-01 1.8E-01 1.8E-01 2.0E-01 1.9E-01 1.9E-01 Citraconic acid 1.4E-03 1.2E-03 1.5E-03 1.3E-03 1.5E-03 1.5E-03 4-Methyl-2-oxovaleric acid / 3-Methyl-2-oxovaleric acid 2.8E-01 2.8E-01 2.9E-01 2.7E-01 2.8E-01 3.0E-01 Heptanoic acid N.D. 2.1E-03 2.4E-03 1.7E-03 2.0E-03 2.6E-03 N-Acetyl-β-alanine 9.7E-03 1.0E-02 8.9E-03 7.5E-03 9.2E-03 1.0E-02 Glutaric acid 4.6E-03 5.2E-03 5.1E-03 4.7E-03 5.2E-03 5.0E-03 Malic acid 1.3E+00 1.3E+00 1.3E+00 1.3E+00 1.4E+00 1.4E+00 Threonic acid 5.0E-02 5.3E-02 5.4E-02 4.7E-02 5.2E-02 5.2E-02 Ethanolamine phosphate 6.1E-03 4.7E-03 3.6E-03 5.8E-03 4.5E-03 3.7E-03 Octanoic acid 1.5E-03 N.D. 2.1E-03 1.8E-03 1.9E-03 2.4E-03 4-Acetamidobutanoic acid 7.7E-04 9.0E-04 7.8E-04 N.D. 7.5E-04 N.D. 2-Oxoglutaric acid 1.6E-01 2.0E-01 2.1E-01 1.6E-01 2.1E-01 2.2E-01 2-Hydroxyglutaric acid 3.4E-02 3.8E-02 3.8E-02 3.2E-02 3.9E-02 4.0E-02 Tartaric acid N.D. N.D. N.D. 7.7E-04 N.D. N.D. Cysteinesulfinic acid 1.9E-02 1.8E-02 1.7E-02 1.9E-02 1.9E-02 1.7E-02 Dihydroorotic acid 1.1E-03 1.5E-03 1.3E-03 9.8E-04 1.4E-03 1.3E-03 Pelargonic acid 6.1E-03 7.1E-03 9.3E-03 5.6E-03 6.9E-03 8.0E-03 3-Hydroxy-3-methylglutaric acid 2.0E-02 2.2E-02 2.2E-02 1.8E-02 1.9E-02 2.0E-02 Terephthalic acid 3.7E-03 3.2E-03 3.6E-03 3.2E-03 3.9E-03 3.7E-03 Phthalic acid N.D. N.D. N.D. 9.0E-04 6.9E-04 N.D. Phosphoenolpyruvic acid 1.6E-02 1.4E-02 9.6E-03 1.6E-02 1.4E-02 9.2E-03 Uric acid 5.5E-04 8.7E-04 4.8E-04 7.7E-04 5.8E-04 5.7E-04 Cysteic acid 1.4E-03 2.0E-03 2.1E-03 1.9E-03 1.8E-03 1.7E-03 Dihydroxyacetone phosphate 2.5E-02 3.4E-02 3.1E-02 2.3E-02 4.9E-02 4.7E-02 Glyceraldehyde 3-phosphate 3.2E-03 1.8E-03 3.5E-03 3.0E-03 4.3E-03 4.7E-03 Glycerol 2-phosphate 1.4E-03 1.6E-03 1.6E-03 1.4E-03 1.5E-03 1.5E-03 Glycerol 3-phosphate 5.9E-02 8.6E-02 9.3E-02 5.8E-02 7.5E-02 8.6E-02 Decanoic acid 2.9E-03 3.6E-03 3.8E-03 3.1E-03 3.5E-03 3.6E-03 Isovalerylalanine / N-Acetylleucine 3.3E-04 4.6E-04 6.6E-04 4.0E-04 5.0E-04 3.1E-04 cis-Aconitic acid 3.3E-02 3.3E-02 3.5E-02 2.9E-02 2.9E-02 3.3E-02 N-Acetylasparagine 3.8E-03 3.1E-03 3.4E-03 2.9E-03 2.7E-03 2.8E-03 N-Acetylaspartic acid 2.5E-01 2.8E-01 2.8E-01 2.8E-01 3.2E-01 3.1E-01 N-Carbamoylaspartic acid 2.3E-02 2.0E-02 1.8E-02 2.4E-02 2.1E-02 1.9E-02 Hippuric acid 1.7E-03 1.6E-03 1.4E-03 1.7E-03 1.5E-03 1.3E-03 O-Phosphoserine 5.1E-03 2.6E-03 2.0E-03 9.1E-03 5.8E-03 3.3E-03 2-Phosphoglyceric acid 5.6E-03 5.4E-03 4.1E-03 6.7E-03 5.5E-03 4.2E-03 3-Phosphoglyceric acid 3.5E-02 3.0E-02 2.3E-02 3.6E-02 3.3E-02 2.1E-02 Undecanoic acid N.D. N.D. N.D. N.D. N.D. N.D. N-Acetylglutamine 2.3E-03 2.4E-03 2.4E-03 1.9E-03 2.4E-03 2.2E-03 Azelaic acid N.D. N.D. N.D. 8.8E-04 N.D. N.D. 10-Hydroxydecanoic acid N.D. N.D. N.D. N.D. N.D. N.D. N-Acetylglutamic acid 6.9E-02 7.5E-02 7.6E-02 7.3E-02 8.4E-02 8.2E-02 Citric acid 5.9E-01 6.1E-01 6.4E-01 5.3E-01 5.6E-01 5.8E-01 Isocitric acid 1.4E-02 1.1E-02 1.2E-02 1.1E-02 N.D. 1.1E-02 Quinic acid 2.2E-03 3.6E-03 2.1E-03 2.8E-03 1.8E-03 1.8E-03 Glucuronic acid/ Galacturonic acid 1.3E-03 1.4E-03 1.3E-03 1.2E-03 1.5E-03 1.8E-03 Gluconic acid 2.0E-02 1.8E-02 1.8E-02 1.7E-02 1.6E-02 1.7E-02 Lauric acid 9.3E-03 7.1E-03 9.0E-03 2.0E-02 8.6E-03 7.7E-03 N2-Acetylaminoadipic acid 3.9E-03 4.3E-03 4.7E-03 5.0E-03 5.1E-03 5.6E-03 Glucaric acid N.D. N.D. N.D. N.D. N.D. N.D. Phosphocreatine 8.5E-02 8.7E-02 7.2E-02 6.9E-02 8.0E-02 6.8E-02 O-Succinylhomoserine 3.9E-03 4.4E-03 4.7E-03 3.6E-03 5.0E-03 4.7E-03 Pantothenic acid 5.7E-02 5.7E-02 5.3E-02 5.3E-02 5.5E-02 4.9E-02 Myristoleic acid 7.2E-04 5.7E-04 5.8E-04 8.2E-04 7.6E-04 8.3E-04 Xylulose 5-phosphate 8.3E-04 7.2E-04 6.9E-04 5.2E-04 8.4E-04 7.5E-04 Ribose 5-phosphate 9.5E-03 8.1E-03 1.1E-02 1.2E-02 1.5E-02 1.6E-02 Ribulose 5-phosphate 1.2E-02 1.5E-02 1.5E-02 1.3E-02 2.0E-02 2.0E-02 2-Deoxyglucose 6-phosphate 3.2E-03 3.4E-03 3.3E-03 3.3E-03 3.0E-03 3.2E-03 Ascorbate 2-phosphate 8.5E-04 8.7E-04 8.2E-04 7.5E-04 8.3E-04 9.0E-04 myo-Inositol 1-phosphate / myo-Inositol 3-phosphate 1.4E-02 1.7E-02 1.6E-02 1.4E-02 1.5E-02 1.5E-02 Glucose 6-phosphate 1.3E-01 2.4E-01 2.4E-01 1.2E-01 2.3E-01 2.6E-01 Fructose 6-phosphate 3.2E-02 6.2E-02 6.5E-02 3.1E-02 6.3E-02 6.5E-02 Glucose 1-phosphate 2.9E-02 4.0E-02 3.9E-02 2.9E-02 4.0E-02 4.2E-02 myo-Inositol 2-phosphate 2.9E-03 2.8E-03 1.7E-03 N.D. N.D. 1.7E-03 Sulfotyrosine N.D. 5.3E-04 N.D. 4.7E-04 3.3E-04 N.D. 2,3-Diphosphoglyceric acid 6.1E-02 7.2E-02 7.2E-02 6.1E-02 7.5E-02 7.2E-02 6-Phosphogluconic acid 7.9E-03 1.5E-02 1.6E-02 8.7E-03 1.7E-02 1.8E-02 Rhein 5.9E-03 6.4E-03 6.4E-03 6.0E-03 6.3E-03 6.4E-03 Sedoheptulose 7-phosphate 1.4E-02 2.0E-02 2.5E-02 N.D. 1.9E-02 2.4E-02 N-Acetylglucosamine 1-phosphate 2.2E-02 2.8E-02 2.5E-02 2.1E-02 2.8E-02 2.4E-02 N-Acetylglucosamine 6-phosphate 6.2E-03 6.6E-03 6.2E-03 5.2E-03 6.2E-03 5.7E-03 cCMP / 2',3'-cCMP 1.1E-03 1.2E-03 1.0E-03 6.5E-04 8.1E-04 1.1E-03 dUMP 2.1E-03 1.9E-03 1.6E-03 1.9E-03 1.8E-03 1.7E-03 N-Acetylneuraminic acid 2.6E-02 3.5E-02 3.9E-02 2.4E-02 3.5E-02 3.8E-02 Ribulose 1,5-diphosphate 5.0E-04 8.8E-04 5.2E-04 4.5E-04 4.1E-04 N.D. dTMP 1.0E-03 1.1E-03 1.2E-03 8.3E-04 1.1E-03 8.9E-04 3'-CMP / 2'-CMP 1.2E-03 1.2E-03 1.2E-03 8.4E-04 7.0E-04 1.1E-03 CMP 4.3E-03 4.8E-03 5.4E-03 4.4E-03 4.6E-03 5.1E-03 UMP 2.4E-02 2.4E-02 2.9E-02 2.1E-02 2.3E-02 2.4E-02 N-Glycolylneuraminic acid 1.2E-03 1.5E-03 1.3E-03 1.1E-03 1.2E-03 1.5E-03 cAMP 2.2E-03 1.9E-03 1.7E-03 2.5E-03 2.3E-03 1.7E-03 Phytic acid_divalent 1.1E-02 1.8E-02 1.9E-02 8.5E-03 1.8E-02 1.9E-02 dAMP 3.0E-04 4.2E-04 3.4E-04 4.1E-04 3.4E-04 3.5E-04 5-Aminoimidazole-4-carboxamide ribotide 3.1E-03 5.1E-03 5.4E-03 5.0E-04 6.8E-04 5.7E-04 Fructose 1,6-diphosphate 6.4E-02 8.3E-02 7.3E-02 6.7E-02 9.1E-02 8.4E-02 AMP 3.6E-02 4.2E-02 5.2E-02 3.9E-02 4.3E-02 4.9E-02 IMP 2.3E-03 2.2E-03 1.9E-03 2.1E-03 2.0E-03 1.9E-03 GMP 6.2E-03 7.3E-03 8.6E-03 6.3E-03 7.4E-03 8.5E-03 XMP 3.6E-04 3.4E-04 3.0E-04 4.3E-04 2.7E-04 N.D. NADPH_divalent 2.2E-02 1.5E-02 1.7E-02 2.6E-02 2.5E-02 2.1E-02 CoA_divalent 2.9E-02 4.2E-02 4.4E-02 3.0E-02 5.0E-02 5.0E-02 dCDP 6.0E-04 7.7E-04 8.0E-04 5.3E-04 6.8E-04 7.5E-04 PRPP 1.7E-01 2.1E-01 2.3E-01 1.6E-01 2.2E-01 2.5E-01 FAD_divalent 6.4E-03 7.3E-03 6.7E-03 6.6E-03 7.3E-03 7.4E-03 dTDP 1.4E-03 1.6E-03 2.3E-03 1.8E-03 1.8E-03 1.8E-03 CDP 9.6E-03 1.1E-02 1.3E-02 1.2E-02 1.1E-02 1.3E-02 UDP 5.2E-02 6.0E-02 7.1E-02 6.0E-02 5.8E-02 6.6E-02 dADP 1.0E-03 7.5E-04 7.7E-04 1.1E-03 8.9E-04 9.0E-04 P1, P4-Di(adenosine-5') tetraphosphate_divalent 7.8E-04 7.4E-04 8.2E-04 7.1E-04 6.4E-04 N.D. Thiamine diphosphate 1.6E-03 1.3E-03 1.3E-03 1.2E-03 1.3E-03 1.4E-03 3-Methylcrotonyl CoA_divalent N.D. 6.2E-04 2.5E-04 3.1E-04 N.D. 5.0E-04 Malonyl CoA_divalent 6.7E-04 6.6E-04 2.8E-04 5.2E-04 N.D. 5.4E-04 Adenosine 5'-phosphosulfate 4.8E-03 5.6E-03 6.2E-03 4.5E-03 6.9E-03 6.7E-03 ADP 1.8E-01 1.9E-01 2.0E-01 2.1E-01 1.8E-01 1.9E-01 3',5'-ADP N.D. 5.5E-04 8.0E-04 6.9E-04 8.0E-04 5.7E-04 Succinyl CoA_divalent / Methylmalonyl CoA_divalent N.D. 6.8E-04 5.6E-04 6.0E-04 7.5E-04 1.0E-03 GDP 1.9E-02 2.0E-02 2.1E-02 2.3E-02 1.8E-02 2.2E-02 HMG CoA_divalent 1.2E-02 1.2E-02 1.1E-02 1.1E-02 1.2E-02 1.2E-02 FMN 6.6E-04 7.5E-04 6.1E-04 N.D. 7.6E-04 7.6E-04 Adenylosuccinic acid 7.5E-04 9.5E-04 1.0E-03 4.4E-04 5.4E-04 4.6E-04 dCTP 1.1E-02 1.1E-02 1.1E-02 1.1E-02 1.2E-02 1.2E-02 dTTP 2.6E-02 2.7E-02 2.7E-02 2.6E-02 3.0E-02 2.8E-02 CTP 1.8E-01 2.0E-01 1.8E-01 1.8E-01 1.9E-01 2.0E-01 UTP 8.3E-01 8.8E-01 8.5E-01 7.8E-01 8.4E-01 8.7E-01 CDP-choline 8.3E-04 9.9E-04 1.2E-03 7.6E-04 9.9E-04 8.0E-04 dATP 1.1E-02 1.2E-02 1.1E-02 1.1E-02 1.2E-02 1.2E-02 ATP 2.5E+00 2.8E+00 2.6E+00 2.4E+00 2.7E+00 2.8E+00 GTP 4.3E-01 4.7E-01 4.4E-01 4.3E-01 4.7E-01 4.8E-01 ADP-ribose 6.1E-03 6.5E-03 8.2E-03 6.8E-03 9.2E-03 1.0E-02 dTDP-glucose 2.3E-03 2.6E-03 2.6E-03 2.3E-03 2.5E-03 2.5E-03 UDP-glucose / UDP-galactose 4.4E-01 4.7E-01 4.5E-01 4.4E-01 4.9E-01 4.8E-01 UDP-glucuronic acid 1.6E-01 2.1E-01 1.9E-01 1.6E-01 2.0E-01 2.0E-01 ADP-glucose / GDP-fucose 1.8E-02 2.5E-02 2.3E-02 1.9E-02 2.4E-02 2.5E-02 GDP-glucose/GDP-mannose/GDP-galactose 1.2E-02 1.7E-02 1.7E-02 1.2E-02 1.7E-02 1.9E-02 UDP-N-acetylgalactosamine / UDP-N-acetylglucosamine 5.2E-01 5.9E-01 5.9E-01 5.0E-01 5.8E-01 5.8E-01 CMP-N-acetylneuraminate 3.6E-02 3.8E-02 3.9E-02 3.4E-02 3.8E-02 3.8E-02 NAD+ 3.0E-01 3.4E-01 3.5E-01 3.0E-01 3.4E-01 3.4E-01 Deamido-NAD+ 1.8E-03 2.0E-03 1.7E-03 1.2E-03 1.4E-03 1.2E-03 NADH 2.6E-02 2.4E-02 2.2E-02 2.3E-02 2.3E-02 2.4E-02 3'-Dephospho CoA 4.7E-04 9.5E-04 1.0E-03 N.D. 8.1E-04 1.3E-03 NADP+ 2.0E-02 3.2E-02 2.7E-02 1.6E-02 2.2E-02 2.8E-02 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name Pyruvic acid Isobutyric acid / Butyric acid Lactic acid Isovaleric acid / Valeric acid 3-Hydroxybutyric acid Glyceric acid Fumaric acid 2-Oxoisovaleric acid Hexanoic acid N-Acetylglycine Succinic acid 2-Hydroxyvaleric acid Isethionic acid 5-Oxoproline Citraconic acid 4-Methyl-2-oxovaleric acid / 3-Methyl-2-oxovaleric acid Heptanoic acid N-Acetyl-β-alanine Glutaric acid Malic acid Threonic acid Ethanolamine phosphate Octanoic acid 4-Acetamidobutanoic acid 2-Oxoglutaric acid 2-Hydroxyglutaric acid Tartaric acid Cysteinesulfinic acid Dihydroorotic acid Pelargonic acid 3-Hydroxy-3-methylglutaric acid Terephthalic acid Phthalic acid Phosphoenolpyruvic acid Uric acid Cysteic acid Dihydroxyacetone phosphate Glyceraldehyde 3-phosphate Glycerol 2-phosphate Glycerol 3-phosphate Decanoic acid Isovalerylalanine / N-Acetylleucine cis-Aconitic acid N-Acetylasparagine N-Acetylaspartic acid N-Carbamoylaspartic acid Hippuric acid O-Phosphoserine 2-Phosphoglyceric acid 3-Phosphoglyceric acid Undecanoic acid N-Acetylglutamine Azelaic acid 10-Hydroxydecanoic acid N-Acetylglutamic acid Citric acid Isocitric acid Quinic acid Glucuronic acid/ Galacturonic acid Gluconic acid Lauric acid N2-Acetylaminoadipic acid Glucaric acid Phosphocreatine O-Succinylhomoserine Pantothenic acid Myristoleic acid Xylulose 5-phosphate Ribose 5-phosphate Ribulose 5-phosphate 2-Deoxyglucose 6-phosphate Ascorbate 2-phosphate myo-Inositol 1-phosphate / myo-Inositol 3-phosphate Glucose 6-phosphate Fructose 6-phosphate Glucose 1-phosphate myo-Inositol 2-phosphate Sulfotyrosine 2,3-Diphosphoglyceric acid 6-Phosphogluconic acid Rhein Sedoheptulose 7-phosphate N-Acetylglucosamine 1-phosphate N-Acetylglucosamine 6-phosphate cCMP / 2',3'-cCMP dUMP N-Acetylneuraminic acid Ribulose 1,5-diphosphate dTMP 3'-CMP / 2'-CMP CMP UMP N-Glycolylneuraminic acid cAMP Phytic acid_divalent dAMP 5-Aminoimidazole-4-carboxamide ribotide Fructose 1,6-diphosphate AMP IMP GMP XMP NADPH_divalent CoA_divalent dCDP PRPP FAD_divalent dTDP CDP UDP dADP P1, P4-Di(adenosine-5') tetraphosphate_divalent Thiamine diphosphate 3-Methylcrotonyl CoA_divalent Malonyl CoA_divalent Adenosine 5'-phosphosulfate ADP 3',5'-ADP Succinyl CoA_divalent / Methylmalonyl CoA_divalent GDP HMG CoA_divalent FMN Adenylosuccinic acid dCTP dTTP CTP UTP CDP-choline dATP ATP GTP ADP-ribose dTDP-glucose UDP-glucose / UDP-galactose UDP-glucuronic acid ADP-glucose / GDP-fucose GDP-glucose/GDP-mannose/GDP-galactose UDP-N-acetylgalactosamine / UDP-N-acetylglucosamine CMP-N-acetylneuraminate NAD+ Deamido-NAD+ NADH 3'-Dephospho CoA NADP+ METABOLITES_END #END