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
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2017-12-11 16:13:42 UTC
HMDB IDHMDB0002302
Secondary Accession Numbers
  • HMDB02302
Metabolite Identification
Common NameIndole-3-propionic acid
DescriptionIndole-3-propionic acid (IPA, indole-3-propionate, or indolepropionic acid), is a deamination product of tryptophan formed by symbiotic bacteria in the gastrointestinal tract of mammals and birds. It is endogenously produced by human microbiota and has only been detected in vivo when the species Clostridium sporogenes is present in the gastrointestinal tract (PMID: 19234110 ). Indole-3-propionic acid is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals that is synthesized by the human body. Similar to melatonin but unlike other antioxidants, indole-3-propionic acid scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds (PMID: 9928448 ). Indole-3-propionic acid has been shown to prevent oxidative stress and death of primary neurons and neuroblastoma cells exposed to the amyloid beta-protein in the form of amyloid fibrils, one of the most prominent neuropathologic features of Alzheimer's disease. Indole-3-propionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress. (PMID: 10319516 ). More recently it has been found that higher indole-3-propionic acid levels in serum/plasma are associated with reduced likelihood of type 2 diabetes and with higher levels of consumption of fiber-rich foods (PMID: 28397877 ).
Structure
Thumb
Synonyms
ValueSource
beta-(3-Indolyl)propionic acidChEBI
Indole-3-propionic acidChEBI
Indolepropionic acidChEBI
b-(3-Indolyl)propionateGenerator
b-(3-Indolyl)propionic acidGenerator
beta-(3-Indolyl)propionateGenerator
β-(3-indolyl)propionateGenerator
β-(3-indolyl)propionic acidGenerator
3-IndolepropionateGenerator
Indole-3-propionateGenerator
IndolepropionateGenerator
1H-Indole-3-propionateHMDB
1H-Indole-3-propionic acidHMDB
3-(1H-indol-3-yl)PropanoateHMDB
3-(1H-indol-3-yl)Propanoic acidHMDB
3-(1H-indol-3-yl)PropionateHMDB
3-(1H-indol-3-yl)Propionic acidHMDB
3-(2-Carboxyethyl)-1H-indoleHMDB
3-(3-Indolyl)propanoateHMDB
3-(3-Indolyl)propanoic acidHMDB
3-(3-Indolyl)propionateHMDB
3-(3-Indolyl)propionic acidHMDB
b-Indole-3-propionateHMDB
b-Indole-3-propionic acidHMDB
b-IndolepropionateHMDB
b-Indolepropionic acidHMDB
beta-Indole-3-propionateHMDB
beta-Indole-3-propionic acidHMDB
beta-IndolepropionateHMDB
beta-Indolepropionic acidHMDB
IPAHMDB
Indole propionateMeSH
Indole-3-propanoic acidMeSH
3-Indolepropionic acidHMDB
Chemical FormulaC11H11NO2
Average Molecular Weight189.2105
Monoisotopic Molecular Weight189.078978601
IUPAC Name3-(1H-indol-3-yl)propanoic acid
Traditional Nameindolylpropionic acid
CAS Registry Number830-96-6
SMILES
OC(=O)CCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
InChI KeyGOLXRNDWAUTYKT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.75HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP2.04ALOGPS
logP2.15ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.05 m³·mol⁻¹ChemAxon
Polarizability20 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-1900000000-7964cf38946a23d63104View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-1900000000-79b70b4d80349fed40a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-8910000000-cc3bf52f2cbb339eea4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-5bf41cc0642ca12d91ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2bdd32c86cd63a03b739View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-8900000000-fa98f64c6c35db6c3425View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-1900000000-7964cf38946a23d63104View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00e9-0900000000-aa04863f4b124d617168View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-c3c14c76cdb38c3798f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-4be398aaf9b927637228View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5f65be50e34cc07d1a77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-2900000000-747697a81c30bbf35e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-76970d017d781fd87474View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-35d9289d5e0f2905c29dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-8a8af8b32271e2d2eef0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-de72f9061ea0bb241ef7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothNormal details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.481 (0.291 - 1.095) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not Quantified Not AvailableNot AvailableNormal details
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothHemodialysis patients with colon details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
SalivaDetected but not Quantified Adult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not Quantified Adult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000941
KNApSAcK IDC00000115
Chemspider ID3613
KEGG Compound IDNot Available
BioCyc IDCPD-85
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6602
PubChem Compound3744
PDB IDIOP
ChEBI ID43580
References
Synthesis ReferenceJohnson, Herbert E.; Crosby, Donald G. 3-Indolepropionic acid. Journal of Organic Chemistry (1960), 25 569-71.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA: Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid. J Biol Chem. 1999 Jul 30;274(31):21937-42. [PubMed:10419516 ]
  2. Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, Siuzdak G: Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3698-703. doi: 10.1073/pnas.0812874106. Epub 2009 Feb 20. [PubMed:19234110 ]
  3. Reiter RJ, Guerrero JM, Garcia JJ, Acuna-Castroviejo D: Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin. Ann N Y Acad Sci. 1998 Nov 20;854:410-24. [PubMed:9928448 ]
  4. Kim WS, Gardan L, Rhim SL, Geider K: Erwinia pyrifoliae sp. nov., a novel pathogen that affects Asian pear trees (Pyrus pyrifolia Nakai) Int J Syst Bacteriol. 1999 Apr;49 Pt 2:899-905. doi: 10.1099/00207713-49-2-899. [PubMed:10319516 ]
  5. de Mello VD, Paananen J, Lindstrom J, Lankinen MA, Shi L, Kuusisto J, Pihlajamaki J, Auriola S, Lehtonen M, Rolandsson O, Bergdahl IA, Nordin E, Ilanne-Parikka P, Keinanen-Kiukaanniemi S, Landberg R, Eriksson JG, Tuomilehto J, Hanhineva K, Uusitupa M: Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study. Sci Rep. 2017 Apr 11;7:46337. doi: 10.1038/srep46337. [PubMed:28397877 ]