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Human Metabolome Database Version 2.5

 

Showing metabocard for 5-Methoxyindoleacetate (HMDB04096)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 11:48:49
Update Date 2009-05-26 11:47:18
Accession Number HMDB04096
Secondary Accession Numbers Not Available
Common Name 5-Methoxyindoleacetate
Description 5-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)
Synonyms
  1. 5-Methoxyindol-3-ylacetate
  2. 5-Methoxyindol-3-ylacetic acid
  3. 5-Methoxyindole-3-acetate
  4. 5-Methoxyindole-3-acetic acid
  5. 5-Methoxyindoleacetate
  6. 5-Methoxyindoleacetic acid
  7. Methoxyindoleacetate
  8. Methoxyindoleacetic acid
Chemical IUPAC Name 2-(5-methoxy-1H-indol-3-yl)acetic acid
Chemical Formula C11H11NO3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Indoles and Indole Derivatives
Sub Class
  • Indole acids
Family
  • Mammalian Metabolite
Species
  • alkyl aryl ether
  • carboxylic acid
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 205.210
Monoisotopic Molecular Weight 205.073898
Isomeric SMILES COC1=CC2=C(NC=C2CC(O)=O)C=C1
Canonical SMILES COC1=CC2=C(NC=C2CC(O)=O)C=C1
KEGG Compound ID C05660 Link Image
BioCyc ID Not Available
BiGG ID 46224 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB04096 Link Image
Metagene Link HMDB04096 Link Image
METLIN ID 7016 Link Image
PubChem Compound 18986 Link Image
PubChem Substance 8164168 Link Image
ChEBI ID Not Available
CAS Registry Number 608-07-1
InChI Identifier InChI=1/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)
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.69699997 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.76 [Predicted by ALOGPS]; 1.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 Link Image map00380 Link Image
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. [PubMed Link Image]
Metabolic Enzymes
  1. Hydroxyindole O-methyltransferase
Enzyme 1 [top]
Enzyme 1 ID 5333
Enzyme 1 Name Hydroxyindole O-methyltransferase
Enzyme 1 Synonyms
  1. HIOMT
  2. Acetylserotonin O-methyltransferase
  3. ASMT
Enzyme 1 Gene Name ASMT
Enzyme 1 Protein Sequence >Hydroxyindole O-methyltransferase 
MGSSEDQAYRLLNDYANGFMVSQVLFAACELGVFDLLAEAPGPLDVAAVAAGVRASAHGT
ELLLDICVSLKLLKVETRGGKAFYRNTELSSDYLTTVSPTSQCSMLKYMGRTSYRCWGHL
ADAVREGRNQYLETFGVPAEELFTAIYRSEGERLQFMQALQEVWSVNGRSVLTAFDLSVF
PLMCDLGGGAGALAKECMSLYPGCKITVFDIPEVVWTAKQHFSFQEEEQIDFQEGDFFKD
PLPEADLYILARVLHDWADGKCSHLLERIYHTCKPGGGILVIESLLDEDRRGPLLTQLYS
LNMLVQTEGQERTPTHYHMLLSSAGFRDFQFKKTGAIYDAILARK
Enzyme 1 Number of Residues 345
Enzyme 1 Molecular Weight 38453
Enzyme 1 Theoretical pI 4.82
Enzyme 1 GO Classification
Function
  • O-methyltransferase activity
  • catalytic activity
  • methyltransferase activity
  • transferase activity
  • transferase activity, transferring one-carbon groups
Process
—
Component
—
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
Enzyme 1 Pathways
Enzyme 1 Reactions
  • S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein Not Available
Enzyme 1 UniProtKB/Swiss-Prot ID P46597 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name HIOM_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID U11098 Link Image
Enzyme 1 GeneCard ID ASMT Link Image
Enzyme 1 GenAtlas ID ASMT Link Image
Enzyme 1 HGNC ID HGNC:750 Link Image
Enzyme 1 Chromosome Location X
Enzyme 1 Locus Xp22.3 or Yp11.3
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Rodriguez IR, Mazuruk K, Schoen TJ, Chader GJ: Structural analysis of the human hydroxyindole-O-methyltransferase gene. Presence of two distinct promoters. J Biol Chem. 1994 Dec 16;269(50):31969-77. [PubMed Link Image]
  2. Donohue SJ, Roseboom PH, Illnerova H, Weller JL, Klein DC: Human hydroxyindole-O-methyltransferase: presence of LINE-1 fragment in a cDNA clone and pineal mRNA. DNA Cell Biol. 1993 Oct;12(8):715-27. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available