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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2020-02-03 17:11:42 UTC
Update Date2020-06-03 15:12:17 UTC
HMDB IDHMDB0240623
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethyl indole-3-propanoate
DescriptionMethyl indole-3-propanoate, also known as methyl indole-3-propionate, 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. Methyl indole-3-propanoate is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 28916042 ).
Structure
Data?1580751494
Synonyms
ValueSource
Methyl 3-(1H-indol-3-yl)propanoic acidGenerator
MIPHMDB
Methyl 1H-indole-3-propanoateHMDB
Methyl 1H-indole-3-propionateHMDB
Methyl 3-(1H-indol-3-yl)propanoateHMDB
Methyl 3-(1H-indol-3-yl)propionateHMDB
Methyl 3-(3-indolyl)propanoateHMDB
Methyl 3-(3-indolyl)propionateHMDB
Methyl 3-(indol-3-yl)propanoateHMDB
Methyl 3-(indol-3-yl)propionateHMDB
Methyl indole-3-propanoateHMDB
Methyl indole-3-propionateHMDB
Chemical FormulaC12H13NO2
Average Molecular Weight203.241
Monoisotopic Molecular Weight203.094628663
IUPAC Namemethyl 3-(1H-indol-3-yl)propanoate
Traditional Namemethyl 3-(1H-indol-3-yl)propanoate
CAS Registry Number5548-09-4
SMILES
COC(=O)CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C12H13NO2/c1-15-12(14)7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,13H,6-7H2,1H3
InChI KeyBAYIDMGOQRXHBC-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Fatty acid ester
  • Substituted pyrrole
  • Benzenoid
  • Fatty acyl
  • Methyl ester
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.93ALOGPS
logP2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)16.16ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.82 m³·mol⁻¹ChemAxon
Polarizability22.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0522 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21711
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pavlova T, Vidova V, Bienertova-Vasku J, Janku P, Almasi M, Klanova J, Spacil Z: Urinary intermediates of tryptophan as indicators of the gut microbial metabolism. Anal Chim Acta. 2017 Sep 22;987:72-80. doi: 10.1016/j.aca.2017.08.022. Epub 2017 Aug 26. [PubMed:28916042 ]