You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 23:07:55 UTC
Update Date2020-05-21 16:28:50 UTC
MCDB ID BMDB0004096
Secondary Accession Numbers
  • BMDB04096
Metabolite Identification
Common Name5-Methoxyindoleacetate
Description5-Methoxyindoleacetate, also known as 5-methoxy-iaa or 5-miaa, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methoxyindoleacetate exists in all living organisms, ranging from bacteria to humans. 5-Methoxyindoleacetate and S-adenosylhomocysteine can be biosynthesized from 5-hydroxyindoleacetic acid and S-adenosylmethionine through the action of the enzyme acetylserotonin O-methyltransferase. In cattle, 5-methoxyindoleacetate is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
2-(5-Methoxy-1H-indol-3-yl)ethanoic acidChEBI
2-(5-Methoxyindole-3-yl)acetic acidChEBI
5-Methoxyindol-3-ylacetic acidChEBI
5-Methoxyindoleacetic acidChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanoateGenerator
2-(5-Methoxyindole-3-yl)acetateGenerator
5-Methoxyindol-3-ylacetateGenerator
5-Methoxyindole-3-acetateHMDB
5-Methoxyindole-3-acetic acidHMDB
MethoxyindoleacetateHMDB
Methoxyindoleacetic acidHMDB
5-Methoxy-1H-indole-3-acetic acidHMDB
(5-Methoxy-1H-indol-3-yl)acetic acidHMDB
2-(5-Methoxy-1H-indol-3-yl)acetic acidHMDB
2-(5-Methoxy-3-indolyl)acetic acidHMDB
5-Methoxy-3-indoleacetic acidHMDB
5-Methoxy-3-indolylacetic acidHMDB
5-Methoxy-iaaHMDB
5-Methyloxyindole-3-acetic acidHMDB
5-MIAAHMDB
Chemical FormulaC11H11NO3
Average Molecular Weight205.2099
Monoisotopic Molecular Weight205.073893223
IUPAC Name2-(5-methoxy-1H-indol-3-yl)acetic acid
Traditional Name5-methoxyindole-3-acetic acid
CAS Registry Number3471-31-6
SMILES
COC1=CC2=C(NC=C2CC(O)=O)C=C1
InChI Identifier
InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)
InChI KeyCOCNDHOPIHDTHK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.76ALOGPS
logP1.55ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.92 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0004096
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023312
KNApSAcK IDNot Available
Chemspider ID17924
KEGG Compound IDC05660
BioCyc IDCPD-12020
BiGG ID46224
Wikipedia LinkNot Available
METLIN ID7016
PubChem Compound18986
PDB IDMYI
ChEBI ID28281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]