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Record Information
Version3.6
Creation Date2006-05-22 14:17:47 UTC
Update Date2016-02-11 01:05:33 UTC
HMDB IDHMDB02302
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Indolepropionic acid
DescriptionIndole-3-propionate (IPA), a deamination product of tryptophan formed by symbiotic bacteria in the gastrointestinal tract of mammals and birds. 3-Indolepropionic 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. 3-Indolepropionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress. (PMID: 10419516 ).
Structure
Thumb
Synonyms
ValueSource
3-IndolepropionicacidChEMBL
Indole-3-propionic acidChEMBL
3-IndolepropionateGenerator
Indole-3-propionateGenerator
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-(3-Indolyl)propionateHMDB
b-(3-Indolyl)propionic acidHMDB
b-Indole-3-propionateHMDB
b-Indole-3-propionic acidHMDB
b-IndolepropionateHMDB
b-Indolepropionic acidHMDB
beta-(3-Indolyl)propionateHMDB
beta-(3-Indolyl)propionic acidHMDB
beta-Indole-3-propionateHMDB
beta-Indole-3-propionic acidHMDB
beta-IndolepropionateHMDB
beta-Indolepropionic acidHMDB
IPAHMDB
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 KeyInChIKey=GOLXRNDWAUTYKT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
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
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.05 m3·mol-1ChemAxon
Polarizability20 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-de72f9061ea0bb241ef7View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.481 (0.291 - 1.095) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothHemodialysis patients with colon details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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
NuGOwiki LinkHMDB02302
Metagene LinkHMDB02302
METLIN ID6602
PubChem Compound3744
PDB IDIOP
ChEBI IDNot Available
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. [10419516 ]