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1H-Indole-3-propanoic acid (FDB000941)

Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2019-11-26 02:55:39 UTC
Primary IDFDB000941
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1H-Indole-3-propanoic 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) [HMDB]. 1H-Indole-3-propanoic acid is found in common pea.
CAS Number830-96-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H11NO2
IUPAC name3-(1H-indol-3-yl)propanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CCC1=CNC2=CC=CC=C12
Average Molecular Weight189.2105
Monoisotopic Molecular Weight189.078978601
Classification
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
  • 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.83%; H 5.86%; N 7.40%; O 16.91%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-de72f9061ea0bb241ef72015-03-01View Spectrum
GC-MS1H-Indole-3-propanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-1900000000-7964cf38946a23d63104Spectrum
GC-MS1H-Indole-3-propanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-1900000000-7964cf38946a23d63104Spectrum
Predicted GC-MS1H-Indole-3-propanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-1900000000-79b70b4d80349fed40a2Spectrum
Predicted GC-MS1H-Indole-3-propanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-8910000000-cc3bf52f2cbb339eea4aSpectrum
Predicted GC-MS1H-Indole-3-propanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-5bf41cc0642ca12d91dd2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2bdd32c86cd63a03b7392012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-8900000000-fa98f64c6c35db6c34252012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-1900000000-7964cf38946a23d631042012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00e9-0900000000-aa04863f4b124d6171682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-c3c14c76cdb38c3798f02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-db653a92384089e7272c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0900000000-2837a9689ebb97e17c892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03di-9400000000-20084f0045f0393dcaad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9500000000-d39c747b7db2e42acefc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-8927c2758d647a804f4a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-282c233baa3c0e5bf3652021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-1e1179cded69a29a50472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-0aaa5de6ae1a4aafa6612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1b79a66b12c3205108c52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0aor-6900000000-909aa5100e4655d542672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9600000000-e85aca97bdac26c3d2582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-003r-4900000000-29142c5171637b4d5e5f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9600000000-bc2ddd9f185d76d60d502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-4be398aaf9b9276372282017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5f65be50e34cc07d1a772017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-2900000000-747697a81c30bbf35e012017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-76970d017d781fd874742017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-35d9289d5e0f2905c29d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-8a8af8b32271e2d2eef02017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
ChemSpider ID3613
ChEMBL IDCHEMBL207225
KEGG Compound IDNot Available
Pubchem Compound ID3744
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02758
HMDB IDHMDB02302
CRC / DFC (Dictionary of Food Compounds) IDBND62-E:BND62-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000115
HET IDIOP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.