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Record Information
Version4.0
Creation Date2006-05-22 14:17:47 UTC
Update Date2017-09-27 08:24:15 UTC
HMDB IDHMDB0002302
Secondary Accession Numbers
  • HMDB02302
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
SynonymsNot Available
Chemical FormulaC11H11NO2
Average Molecular Weight189.2105
Monoisotopic Molecular Weight189.078978601
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number830-96-6
SMILESNot Available
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
ClassificationNot classified
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 PropertiesNot Available
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
No entries found
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 ]