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Human Metabolome Database Version 3.5

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Showing metabocard for Pyruvic acid (HMDB00243)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:09 -0700
HMDB ID HMDB00243
Secondary Accession Numbers None
Metabolite Identification
Common Name Pyruvic acid
Description Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Oxopropanoate
  2. 2-Oxopropanoic acid
  3. 2-Oxopropionate
  4. 2-Oxopropionic acid
  5. a-Ketopropionate
  6. a-Ketopropionic acid
  7. Acetylformate
  8. Acetylformic acid
  9. alpha-Ketopropionate
  10. alpha-Ketopropionic acid
  11. BTS
  12. Pyroracemate
  13. Pyroracemic acid
  14. Pyruvate
Chemical Formula C3H4O3
Average Molecular Weight 88.0621
Monoisotopic Molecular Weight 88.016043994
IUPAC Name 2-oxopropanoic acid
Traditional IUPAC Name pyruvic acid
CAS Registry Number 127-17-3
SMILES CC(=O)C(O)=O
InChI Identifier InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
InChI Key LCTONWCANYUPML-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Keto-Acids and Derivatives
Sub Class Alpha Keto-Acids and Derivatives
Other Descriptors
  • 2-oxo monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Oxo fatty acids(Lipidmaps)
Substituents
  • Carboxylic Acid
  • Ketone
Direct Parent Alpha Keto-Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Anti-oxidant
  • Component of Alanine and aspartate metabolism
  • Component of Butanoate metabolism
  • Component of Cysteine metabolism
  • Component of Glutamate metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Phenylalanine, tyrosine and tryptophan biosynthesis
  • Component of Propanoate metabolism
  • Component of Purine metabolism
  • Component of Pyruvate metabolism
  • Component of Valine, leucine and isoleucine biosynthesis
  • Energy source
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 13.8 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 134 g/L ALOGPS
LogP -0.38 ALOGPS
LogP 0.066 ChemAxon
LogS 0.18 ALOGPS
pKa (strongest acidic) 2.93 ChemAxon
pKa (strongest basic) -9.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 17.99 ChemAxon
Polarizability 7.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Neuron
  • Pancreas
  • Testes
  • Kidney
  • Liver
  • Thyroid Gland
  • Brain
  • Adipose Tissue
  • Spleen
  • Myocardium
Pathways
Name SMPDB Link KEGG Link
Urea Cycle SMP00059 map00330 Link_out
Glucose-Alanine Cycle SMP00127 Not Available
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Pyruvate Metabolism SMP00060 map00620 Link_out
Alanine Metabolism SMP00055 map00250 Link_out
Ammonia Recycling SMP00009 map00910 Link_out
Glycolysis SMP00040 map00010 Link_out
Citric Acid Cycle SMP00057 map00020 Link_out
Cysteine Metabolism SMP00013 map00270 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Pyruvaldehyde Degradation SMP00459 Not Available
Transfer of Acetyl Groups into Mitochondria SMP00466 Not Available
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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34.5 +/- 25.2 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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64 (22-258) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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81.0 +/- 34.0 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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76.0 +/- 10.0 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
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63.0 +/- 25.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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75.5 (10.0-141.0) uM Newborn (0-30 days old) Not Specified Normal Not Available
Blood Detected and Quantified
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64 (28-145) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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64 (29-144) uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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67 (27-164) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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64 (29-144) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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66 (34-117) uM Elderly (>65 years old) Both Normal Not Available
Blood Detected and Quantified
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93.5 (27.0-160.0) uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
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77.0 (27.0-127) uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
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360 (350-370) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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153.0 (121.0-185.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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53 +/- 42 uM Not Specified Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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71.0 +/- 31.0 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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115.0 +/- 17.0 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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136.0 +/- 29.0 uM Children (1-13 year old) Both Normal Not Available
Saliva Detected and Quantified
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5350 (100-10600) uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
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1-128 uM Adult (>18 years old) Male normal At rest without stimulation
Saliva Detected and Quantified
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1-76 uM Adult (>18 years old) Male normal Salivary induction with a citric acid solution...
Urine Detected and Quantified
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9.79 +/- 9.34 umol/mmol creatinine Infant (0-1 year old) Not Specified Normal Not Available
Urine Detected and Quantified
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2.1 (1.0-3.7) umol/mmol creatinine Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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2.27-79.53 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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4.21 +/- 1.37 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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1.7985 (0-3.597) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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5.4 (2.6-7.9) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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2.7 (0.8-6.4) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal After green tea sonsumption
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal After black tea sonsumption
Urine Detected and Quantified
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21.2 (8.8-59.3) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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28.6 (12.9-43.0) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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12.4 (5.3-22.1) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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10.2 (4.7-40.5) umol/mmol creatinine Adolescent (13-18 years old) Both Normal Not Available
Urine Detected and Quantified
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38.50 (18.32 – 69.64) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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2.13 (0.54-8.67) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
1.68 (0.62-3.30) umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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7 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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50.2 +/- 40 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Cellular Cytoplasm Detected and Quantified
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140 (130-150) uM Adult (>18 years old) Both Anoxia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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195.0 (175.0-215.0) uM Adult (>18 years old) Both Meningitis Bacterial
Urine Detected and Quantified
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0.2 (0.10-0.30) umol/mmol creatinine Adult (>18 years old) Both 3-Methylglutaconic Aciduria (TYPE II), X-LINKED Not Available
Urine Detected and Quantified
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45.58 (18.06 – 104.62) umol/mmol creatinine Adult (>18 years old) Both Type 1 diabetes Mellitus Not Available
Associated Disorders and Diseases
Disease References
Anoxia
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834 Link_out
    Meningitis
    • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241 Link_out
      3-methylglutaconic aciduria type II, X-linked
        • http://www.metagene.de/program/d.prg?mp=3-METHYLGLUTACONIC%20ACIDURIA%20(TYPE%20II),%20X-LINKED
        Associated OMIM IDs
        • 302060 Link_out (3-methylglutaconic aciduria type II, X-linked)
        DrugBank ID DB00119 Link_out
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB008293
        KNApSAcK ID C00001200 Link_out
        Chemspider ID 1031 Link_out
        KEGG Compound ID C00022 Link_out
        BioCyc ID PYRUVATE Link_out
        BiGG ID 33546 Link_out
        Wikipedia Link Pyruvic acid Link_out
        NuGOwiki Link HMDB00243 Link_out
        Metagene Link HMDB00243 Link_out
        METLIN ID 117 Link_out
        PubChem Compound 1060 Link_out
        PDB ID PYR Link_out
        ChEBI ID 32816 Link_out
        References
        Synthesis Reference Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.
        Material Safety Data Sheet (MSDS) Download (PDF)
        General References
        1. Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. Pubmed: 7819686 Link_out
        2. Ka T, Yamamoto T, Moriwaki Y, Kaya M, Tsujita J, Takahashi S, Tsutsumi Z, Fukuchi M, Hada T: Effect of exercise and beer on the plasma concentration and urinary excretion of purine bases. J Rheumatol. 2003 May;30(5):1036-42. Pubmed: 12734903 Link_out
        3. Talseth T, Haegele KD, McNay JL, Skrdlant HB, Clementi WA, Shepherd AM: Pharmacokinetics and cardiovascular effects in rabbits of a major hydralazine metabolite, the hydralazine pyruvic-acid hydrazone. J Pharmacol Exp Ther. 1979 Dec;211(3):509-13. Pubmed: 512915 Link_out
        4. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241 Link_out
        5. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834 Link_out
        6. Reece PA, Cozamanis I, Zacest R: Selective high-performance liquid chromatographic assays for hydralazine and its metabolites in plasma of man. J Chromatogr. 1980 Mar 14;181(3-4):427-40. Pubmed: 7391156 Link_out
        7. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979 Link_out
        8. Meijer-Severs GJ, Van Santen E, Meijer BC: Short-chain fatty acid and organic acid concentrations in feces of healthy human volunteers and their correlations with anaerobe cultural counts during systemic ceftriaxone administration. Scand J Gastroenterol. 1990 Jul;25(7):698-704. Pubmed: 2396083 Link_out
        9. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436 Link_out
        10. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454 Link_out
        11. Elling D, Bader K: [Biochemical changes in cervix mucus in stepwise malignant transformation of cervix epithelium] Zentralbl Gynakol. 1990;112(9):555-60. Pubmed: 2378186 Link_out
        12. Mongan PD, Capacchione J, West S, Karaian J, Dubois D, Keneally R, Sharma P: Pyruvate improves redox status and decreases indicators of hepatic apoptosis during hemorrhagic shock in swine. Am J Physiol Heart Circ Physiol. 2002 Oct;283(4):H1634-44. Epub 2002 Jun 20. Pubmed: 12234818 Link_out
        13. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012 Link_out
        14. Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72. Pubmed: 688619 Link_out
        15. Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. Pubmed: 6581765 Link_out
        Enzymes
        Name: Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
        Reactions:
        • pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine = [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO2 [RN:R01699]
        Gene Name: PDHB
        Uniprot ID: P11177 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pyruvate carboxylase, mitochondrial
        Reactions:
        • ATP + pyruvate + HCO3- = ADP + phosphate + oxaloacetate [RN:R00344]
        Gene Name: PC
        Uniprot ID: P11498 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
        Reactions:
        • pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine = [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO2 [RN:R01699]
        Gene Name: PDHA1
        Uniprot ID: P08559 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial
        Reactions:
        • pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine = [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO2 [RN:R01699]
        Gene Name: PDHA2
        Uniprot ID: P29803 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Dihydrolipoyl dehydrogenase, mitochondrial
        Reactions:
        • protein N6-(dihydrolipoyl)lysine + NAD+ = protein N6-(lipoyl)lysine + NADH + H+ [RN:R08550]
        Gene Name: DLD
        Uniprot ID: P09622 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
        Reactions:
        • acetyl-CoA + enzyme N6-(dihydrolipoyl)lysine = CoA + enzyme N6-(S-acetyldihydrolipoyl)lysine [RN:R02569]
        Gene Name: DLAT
        Uniprot ID: P10515 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: D-amino-acid oxidase
        Reactions:
        • a D-amino acid + H2O + O2 = a 2-oxo acid + NH3 + H2O2 [RN:R01340]
        Gene Name: DAO
        Uniprot ID: P14920 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 4-aminobutyrate aminotransferase, mitochondrial
        Reactions:
        • (S)-3-amino-2-methylpropanoate + 2-oxoglutarate = 2-methyl-3-oxopropanoate + L-glutamate
        Gene Name: ABAT
        Uniprot ID: P80404 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Alanine--glyoxylate aminotransferase 2, mitochondrial
        Reactions:
        • L-alanine + glyoxylate = pyruvate + glycine [RN:R00369]
        Gene Name: AGXT2
        Uniprot ID: Q9BYV1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: S-adenosylmethionine decarboxylase proenzyme
        Reactions:
        • S-adenosyl-L-methionine = (5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt + CO2 [RN:R00178]
        Gene Name: AMD1
        Uniprot ID: P17707 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cystathionine gamma-lyase
        Reactions:
        • (1) L-cystathionine + H2O = L-cysteine + NH3 + 2-oxobutanoate (overall reaction) [RN:R01001]
        • (2) (1a) L-cystathionine = L-cysteine + 2-ammoniobut-2-enoate [RN:R08632]
        • (3) (1b) 2-ammoniobut-2-enoate + H2O = 2-oxobutanoate + NH3 (spontaneous) [RN:R08637]
        Gene Name: CTH
        Uniprot ID: P32929 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: L-serine dehydratase/L-threonine deaminase
        Reactions:
        • L-threonine = 2-oxobutanoate + NH3 [RN:R00996]
        Gene Name: SDS
        Uniprot ID: P20132 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 7
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY7
        Uniprot ID: P51828 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 4
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY4
        Uniprot ID: Q8NFM4 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 6
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY6
        Uniprot ID: O43306 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 5
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY5
        Uniprot ID: O95622 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 8
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY8
        Uniprot ID: P40145 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 9
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY9
        Uniprot ID: O60503 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 3
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY3
        Uniprot ID: O60266 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 1
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY1
        Uniprot ID: Q08828 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pyruvate kinase isozymes M1/M2
        Reactions:
        • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
        Gene Name: PKM2
        Uniprot ID: P14618 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pyruvate kinase isozymes R/L
        Reactions:
        • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
        Gene Name: PKLR
        Uniprot ID: P30613 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 3-mercaptopyruvate sulfurtransferase
        Reactions:
        • 3-mercaptopyruvate + cyanide = pyruvate + thiocyanate [RN:R03106]
        Gene Name: MPST
        Uniprot ID: P25325 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Serine--pyruvate aminotransferase
        Reactions:
        • L-serine + pyruvate = 3-hydroxypyruvate + L-alanine [RN:R00585]
        Gene Name: AGXT
        Uniprot ID: P21549 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Alanine aminotransferase 1
        Reactions:
        • L-alanine + 2-oxoglutarate = pyruvate + L-glutamate [RN:R00258]
        Gene Name: GPT
        Uniprot ID: P24298 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: NADP-dependent malic enzyme
        Reactions:
        • (S)-malate + NADP+ = pyruvate + CO2 + NADPH [RN:R00216]
        Gene Name: ME1
        Uniprot ID: P48163 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: NADP-dependent malic enzyme, mitochondrial
        Reactions:
        • (S)-malate + NADP+ = pyruvate + CO2 + NADPH [RN:R00216]
        Gene Name: ME3
        Uniprot ID: Q16798 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: NAD-dependent malic enzyme, mitochondrial
        Reactions:
        • (S)-malate + NAD+ = pyruvate + CO2 + NADH [RN:R00214]
        Gene Name: ME2
        Uniprot ID: P23368 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histidine decarboxylase
        Reactions:
        • L-histidine = histamine + CO2 [RN:R01167]
        Gene Name: HDC
        Uniprot ID: P19113 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: L-lactate dehydrogenase A-like 6A
        Reactions:
        • (S)-lactate + NAD+ = pyruvate + NADH + H+ [RN:R00703]
        Gene Name: LDHAL6A
        Uniprot ID: Q6ZMR3 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylate cyclase type 2
        Reactions:
        • ATP = 3',5'-cyclic AMP + diphosphate [RN:R00089]
        Gene Name: ADCY2
        Uniprot ID: Q08462 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Monocarboxylate transporter 3
        Reactions:
        • --- []
        Gene Name: SLC16A8
        Uniprot ID: O95907 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Monocarboxylate transporter 7
        Reactions:
          Gene Name: SLC16A6
          Uniprot ID: O15403 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Monocarboxylate transporter 6
          Reactions:
            Gene Name: SLC16A5
            Uniprot ID: O15375 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Monocarboxylate transporter 5
            Reactions:
              Gene Name: SLC16A4
              Uniprot ID: O15374 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Phosphatidylserine decarboxylase proenzyme
              Reactions:
              • phosphatidyl-L-serine = phosphatidylethanolamine + CO2 [RN:R02055]
              Gene Name: PISD
              Uniprot ID: Q9UG56 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Probable D-lactate dehydrogenase, mitochondrial
              Reactions:
              • (R)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c [RN:R00197]
              Gene Name: LDHD
              Uniprot ID: Q86WU2 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Alanine aminotransferase 2
              Reactions:
              • L-alanine + 2-oxoglutarate = pyruvate + L-glutamate [RN:R00258]
              Gene Name: GPT2
              Uniprot ID: Q8TD30 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: N-acetylneuraminate lyase
              Reactions:
              • N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate [RN:R01811]
              Gene Name: NPL
              Uniprot ID: Q9BXD5 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Acetolactate synthase-like protein
              Reactions:
                Gene Name: ILVBL
                Uniprot ID: A1L0T0 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Malic enzyme
                Reactions:
                  Gene Name: ME3
                  Uniprot ID: Q8TBJ0 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Transporters
                  Name: Monocarboxylate transporter 4
                  Reactions:
                  • --- []
                  Gene Name: SLC16A3
                  Uniprot ID: O15427 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Monocarboxylate transporter 1
                  Reactions:
                  • --- []
                  Gene Name: SLC16A1
                  Uniprot ID: P53985 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Monocarboxylate transporter 8
                  Reactions:
                  • --- []
                  Gene Name: SLC16A2
                  Uniprot ID: P36021 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Monocarboxylate transporter 2
                  Reactions:
                  • --- []
                  Gene Name: SLC16A7
                  Uniprot ID: O60669 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Monocarboxylate transporter 10
                  Reactions:
                    Gene Name: SLC16A10
                    Uniprot ID: Q8TF71 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Solute carrier organic anion transporter family member 2A1
                    Reactions:
                    • Bicarbonate[c] + Prostaglandin E1[e] <==> Bicarbonate[e] + Prostaglandin E1[c]
                    Gene Name: SLCO2A1
                    Uniprot ID: Q92959 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA