Indole-3-pyruvic acid (CHEM017771)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:37:23 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017771
Identification
Common NameIndole-3-pyruvic acid
ClassSmall Molecule
DescriptionA 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Indole-3-pyruvic acidChEBI
Indolepyruvic acidChEBI
(indol-3-yl)PyruvateKegg
Indole-3-pyruvateKegg
3-(indol-3-yl)PyruvateKegg
(indol-3-yl)Pyruvic acidGenerator
3-(indol-3-yl)Pyruvic acidGenerator
Indol-3-yl pyruvic acidMeSH
1H-Indole-3-pyruvic acidHMDB
3-(1H-Indol-3-yl)-2-oxopropanoic acidHMDB
3-(1H-Indol-3-yl)-2-oxopropionic acidHMDB
3-(3-Indolyl)-2-oxopropanoic acidHMDB
3-(3-Indolyl)-2-oxopropionic acidHMDB
3-(3-Indolyl)pyruvic acidHMDB
3-Indole-2-oxopropanoateHMDB
3-Indole-2-oxopropionateHMDB
3-Indolylpyroracemic acidHMDB
3-Indolylpyruvic acidHMDB
IPAHMDB
IndolepyruvateHMDB
Indolyl-3-pyruvateHMDB
alpha-Oxo-1H-indole-3-propanoic acidHMDB
alpha-Oxo-1H-indole-3-propionic acidHMDB
beta-Indolepyruvic acidHMDB
beta-Indolylpyruvic acidHMDB
α-Oxo-1H-indole-3-propanoic acidHMDB
α-Oxo-1H-indole-3-propionic acidHMDB
β-Indolepyruvic acidHMDB
β-Indolylpyruvic acidHMDB
Chemical FormulaC11H9NO3
Average Molecular Mass203.194 g/mol
Monoisotopic Mass203.058 g/mol
CAS Registry Number392-12-1
IUPAC Name3-(1H-indol-3-yl)-2-oxopropanoic acid
Traditional Name3-(indol-3-yl)pyruvic acid
SMILESOC(=O)C(=O)CC1=CNC2=CC=CC=C12
InChI IdentifierInChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
InChI KeyRSTKLPZEZYGQPY-UHFFFAOYSA-N
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
Substituents
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.71ALOGPS
logP2ChemAxon
logS-2.9ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-9000000000-5abe3dfa1099f9120dc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0159-0900000000-834e4f99d90f0191c044Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-41e6877cb3fb43b1168aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-3900000000-fb0ea14a3950fc521db6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9600000000-a27b1097894cd1feee71Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000t-8900000000-4e6c79f47d063707a802Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8690000000-da9c2a121361518b150fSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0920000000-8595f51ed999e0bf6781Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2f350b1510e9e5627089Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ugi-2900000000-13dc3bda25eafed55bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-e09b4e8b59ee5b205060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-2910000000-93256dde3bb34cbaf5daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-070485cd4db1ed2925ccSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060484
FooDB IDFDB030941
Phenol Explorer IDNot Available
KNApSAcK IDC00007571
BiGG IDNot Available
BioCyc IDINDOLE_PYRUVATE
METLIN IDNot Available
PDB ID3IO
Wikipedia LinkNot Available
Chemspider ID781
ChEBI ID29750
PubChem Compound ID803
Kegg Compound IDC00331
YMDB IDYMDB00169
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12902239
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24445491
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25036485
4. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.
5. 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.
6. 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.
7. 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.
8. 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.