You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2013-05-17 01:24:10 UTC
Update Date2019-07-23 07:14:26 UTC
Secondary Accession Numbers
  • HMDB60484
Metabolite Identification
Common NameIndolepyruvate
DescriptionThe thiamin diphosphate (ThDP)-dependent enzyme indolepyruvate decarboxylase (IPDC) is involved in the biosynthetic pathway of the phytohormone 3-indoleacetic acid and catalyzes the nonoxidative decarboxylation of 3-indolepyruvate to 3-indoleacetaldehyde and carbon dioxide. (PMID: 15835904 ) In addition, the enzyme was compared with the phenylpyruvate decarboxylase from Azospirillum brasilense and the indolepyruvate decarboxylase from Enterobacter cloacae. (PMID: 21501384 ) Indole-3-pyruvate is a microbial metabolite, urinary indole-3-pyruvate is produced by Clostridium sporogenes (PMID: 29168502 ) and Trypanasoma brucei (PMID: 27856732 ).
Indole-3-pyruvic acidChEBI
Indolepyruvic acidChEBI
(indol-3-yl)Pyruvic acidGenerator
3-(indol-3-yl)Pyruvic acidGenerator
indol-3-yl Pyruvic acidMeSH
Chemical FormulaC11H9NO3
Average Molecular Weight203.1941
Monoisotopic Molecular Weight203.058243159
IUPAC Name3-(1H-indol-3-yl)-2-oxopropanoic acid
Traditional Name3-(indol-3-yl)pyruvic acid
CAS Registry Number35656-49-6
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Indole
  • Alpha-keto acid
  • Keto acid
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydroxy ketone
  • Pyrrole
  • Heteroaromatic compound
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors


Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.24 g/LALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.8 m³·mol⁻¹ChemAxon
Polarizability19.72 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0fai-7893000000-84ffd1f401950f7c3032Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0ugi-3794000000-a5d8cc3579802f2ca961Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fai-7893000000-84ffd1f401950f7c3032Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ugi-3794000000-a5d8cc3579802f2ca961Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fai-1931000000-16c0a60dd32e65b8873aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-3900000000-a55cf7c697b6ffbaee85Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-7590000000-c3dd0d149f021914d6e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-1ec34b082b3a3f565a12Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0970000000-e68c2677119696ab9346Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-0900000000-2b64ec50aa8f1360ff4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-ea3949db3c6da8240de8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-4900000000-95c91da39b950494114aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2920000000-9230f7ccfaaaffa71949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f80-0930000000-593d7099407afc68b969Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o9-0900000000-2ad84f63cbf77a1baa8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-6368dc05fa719d5e285aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1590000000-279e5b29f5fe92cccc07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-1910000000-8f926dbcc372f4b220f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-2900000000-431d30e582a7ac0a4805Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030941
KNApSAcK IDC00007571
Chemspider ID781
KEGG Compound IDC00331
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound803
ChEBI ID29750
Food Biomarker OntologyNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Schutz A, Golbik R, Konig S, Hubner G, Tittmann K: Intermediates and transition states in thiamin diphosphate-dependent decarboxylases. A kinetic and NMR study on wild-type indolepyruvate decarboxylase and variants using indolepyruvate, benzoylformate, and pyruvate as substrates. Biochemistry. 2005 Apr 26;44(16):6164-79. [PubMed:15835904 ]
  3. Kneen MM, Stan R, Yep A, Tyler RP, Saehuan C, McLeish MJ: Characterization of a thiamin diphosphate-dependent phenylpyruvate decarboxylase from Saccharomyces cerevisiae. FEBS J. 2011 Jun;278(11):1842-53. doi: 10.1111/j.1742-4658.2011.08103.x. Epub 2011 Apr 18. [PubMed:21501384 ]
  4. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
  5. McGettrick AF, Corcoran SE, Barry PJ, McFarland J, Cres C, Curtis AM, Franklin E, Corr SC, Mok KH, Cummins EP, Taylor CT, O'Neill LA, Nolan DP: Trypanosoma brucei metabolite indolepyruvate decreases HIF-1alpha and glycolysis in macrophages as a mechanism of innate immune evasion. Proc Natl Acad Sci U S A. 2016 Nov 29;113(48):E7778-E7787. doi: 10.1073/pnas.1608221113. Epub 2016 Nov 15. [PubMed:27856732 ]


General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
L-Tryptophan + Water + Oxygen → Indolepyruvate + Ammonia + Hydrogen peroxidedetails