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Record Information
Version3.6
Creation Date2006-08-13 10:48:49 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04096
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Methoxyindoleacetate
Description5-methoxyindoleacetic acid(5-MIAA) is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 micro g/mL using gas chromatography-mass spectrometry.(PMID: 12908946 ). There is increase in urinary 5-MIAA-excretion was shown in patients with cancer of the stomach, rectum and lung. (PMID: 2446428 ).
Structure
Thumb
Synonyms
ValueSource
5-Methoxyindoleacetic acidKegg
5-MethoxyindoleacetateGenerator
2-(5-Methoxy-1H-indol-3-yl)acetateGenerator
5-Methoxyindol-3-ylacetateHMDB
5-Methoxyindol-3-ylacetic acidHMDB
5-Methoxyindole-3-acetateHMDB
5-Methoxyindole-3-acetic acidHMDB
MethoxyindoleacetateHMDB
Methoxyindoleacetic acidHMDB
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 Number608-07-1
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 KeyInChIKey=COCNDHOPIHDTHK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These 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
  • Hydroxyindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.92 m3·mol-1ChemAxon
Polarizability20.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1492000000-4bb4e49122eeca577f6fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.09 +/- 2.13 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
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 IDFDB023312
KNApSAcK IDNot Available
Chemspider ID17924
KEGG Compound IDC05660
BioCyc IDNot Available
BiGG ID46224
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04096
Metagene LinkHMDB04096
METLIN ID7016
PubChem Compound18986
PDB IDMYI
ChEBI ID235589
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Higa S, Markey SP: Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Anal Biochem. 1985 Jan;144(1):86-93. [2580458 ]
  2. Meatherall R, Sharma P: Foxy, a designer tryptamine hallucinogen. J Anal Toxicol. 2003 Jul-Aug;27(5):313-7. [12908946 ]
  3. Sergeeva TI, Raushenbakh TI, Shevchenko MO, Rybal'chenko VG: [Excretion of 5-hydroxyindole-3-acetic and 5-methoxyindole-3-acetic acids in cancer patients]. Vopr Onkol. 1987;33(10):20-5. [2446428 ]

Enzymes

General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Reactions
S-Adenosylmethionine + 5-Hydroxyindoleacetic acid → S-Adenosylhomocysteine + 5-Methoxyindoleacetatedetails