Record Information
Version3.6
Creation Date2006-08-13 10:19:52 UTC
Update Date2013-02-09 00:12:58 UTC
HMDB IDHMDB04073
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxyindoleacetaldehyde
Description5-Hydroxyindoleacetaldehyde is a biogenic aldehyde of serotonin derived from the action of monoamine oxidase (MAO). (PMIDs 11306106, 2470392).
Structure
Thumb
Synonyms
  1. (5-hydroxy-1H-indol-3-yl)acetaldehyde
  2. (5-hydroxyindol-3-yl)acetaldehyde
  3. 5-Hial
  4. 5-Hydroxy-1H-Indole-3-acetaldehyde
  5. 5-Hydroxyindole-3-acetaldehyde
  6. Hydroxyindoleacetaldehyde
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
Traditional IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
CAS Registry Number1892-21-3
SMILES
OC1=CC2=C(NC=C2CC=O)C=C1
InChI Identifier
InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2
InChI KeyOBFAPCIUSYHFIE-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIndoles
Sub ClassN/A
Other Descriptors
  • a small molecule(Cyc)
  • hydroxyindole(ChEBI)
  • indoleacetaldehyde(ChEBI)
Substituents
  • Aldehyde
  • Phenol
  • Phenol Derivative
  • Pyrrole
Direct ParentIndoles
Ontology
StatusExpected and Not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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 solubility1.32 g/LALOGPS
logP1.93ALOGPS
logP1.25ChemAxon
logS-2.1ALOGPS
pKa (strongest acidic)9.55ChemAxon
pKa (strongest basic)-5.5ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area53.09ChemAxon
rotatable bond count2ChemAxon
refractivity49.51ChemAxon
polarizability17.85ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00564
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023299
KNApSAcK IDNot Available
Chemspider ID67261
KEGG Compound IDC05634
BioCyc IDNot Available
BiGG ID46165
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04073
Metagene LinkHMDB04073
METLIN IDNot Available
PubChem Compound74688
PDB IDNot Available
ChEBI ID50157
References
Synthesis ReferenceMarchand, B.; Streffer, Ch. Synthesis of 5-hydroxy-3-indolylacetaldehyde. Angew. Chem. (1959), 71 575.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Some M, Svensson S, Hoog JO, Helander A: Studies on the interaction between ethanol and serotonin metabolism in rat, using deuterated ethanol and 4-methylpyrazole. Biochem Pharmacol. 2000 Feb 15;59(4):385-91. Pubmed: 10644046

Enzymes

Gene Name:
AOX1
Uniprot ID:
Q06278
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
Gene Name:
MAOB
Uniprot ID:
P27338
Reactions
Serotonin + Water + Oxygen unknown 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
MAOA
Uniprot ID:
P21397
Reactions
Serotonin + Water + Oxygen unknown 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
INMT
Uniprot ID:
O95050
Gene Name:
PRMT3
Uniprot ID:
O60678