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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Indolepropionic acid (HMDB02302)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:47 -0600
Update Date 2013-02-08 17:11:42 -0700
HMDB ID HMDB02302
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Indolepropionic acid
Description Indole-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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1H-Indole-3-propionate
  2. 1H-Indole-3-propionic acid
  3. 3-(1H-Indol-3-yl)propanoate
  4. 3-(1H-Indol-3-yl)propanoic acid
  5. 3-(1H-Indol-3-yl)propionate
  6. 3-(1H-Indol-3-yl)propionic acid
  7. 3-(2-Carboxyethyl)-1H-indole
  8. 3-(3-Indolyl)propanoate
  9. 3-(3-Indolyl)propanoic acid
  10. 3-(3-Indolyl)propionate
  11. 3-(3-Indolyl)propionic acid
  12. 3-Indolepropionate
  13. b-(3-Indolyl)propionate
  14. b-(3-Indolyl)propionic acid
  15. b-Indole-3-propionate
  16. b-Indole-3-propionic acid
  17. b-Indolepropionate
  18. b-Indolepropionic acid
  19. beta-(3-Indolyl)propionate
  20. beta-(3-Indolyl)propionic acid
  21. beta-Indole-3-propionate
  22. beta-Indole-3-propionic acid
  23. beta-Indolepropionate
  24. beta-Indolepropionic acid
  25. Indole-3-propionic acid
  26. IPA
Chemical Formula C11H11NO2
Average Molecular Weight 189.2105
Monoisotopic Molecular Weight 189.078978601
IUPAC Name 3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC Name 3-(1H-indol-3-yl)propanoic acid
CAS Registry Number 830-96-6
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 Key GOLXRNDWAUTYKT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Indolyl Carboxylic Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxylic Acid
  • Pyrrole
Direct Parent Indolyl Carboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 134 - 135 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 1.75 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.73 g/L ALOGPS
LogP 2.04 ALOGPS
LogP 2.15 ChemAxon
LogS -2.42 ALOGPS
pKa (strongest acidic) 4.8 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 53.09 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 53.05 ChemAxon
Polarizability 19.93 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (Unknown)
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.481 (0.291 - 1.095) uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and not Quantified
Article_icon
Not Applicable Not Available Not Available Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000941
KNApSAcK ID C00000115 Link_out
Chemspider ID 3613 Link_out
KEGG Compound ID Not Available
BioCyc ID CPD-85 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02302 Link_out
Metagene Link HMDB02302 Link_out
METLIN ID 6602 Link_out
PubChem Compound 3744 Link_out
PDB ID IOP Link_out
ChEBI ID Not Available
References
Synthesis Reference Johnson, 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 Not Available