5-hydroxyindole acetaldehyde (PAMDB120376)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120376
Identification
Name: 5-hydroxyindole acetaldehyde
Description:An aldehyde that is acetaldehyde substituted by a 5-hydroxyindol-3-yl group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (5-hydroxyindol-3-yl)acetaldehyde
  • 5-Hial
  • 5-Hydroxyindole-3-acetaldehyde
  • 5-Hydroxyindoleacetaldehyde
Chemical Formula: C10H9NO2
Average Molecular Weight: 175.187
Monoisotopic Molecular Weight: 175.06332
InChI Key: OBFAPCIUSYHFIE-UHFFFAOYSA-N
InChI: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
CAS number: 1892-21-3
IUPAC Name:(5-hydroxy-1H-indol-3-yl)acetaldehyde
Traditional IUPAC Name: hydroxyindoleacetaldehyde
SMILES:C1(NC2(C(C(CC=O)=1)=CC(=CC=2)O))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct Parent Hydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydrogen aldehyde
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.32 mg/mLALOGPS
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 Area53.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.51 m3·mol-1ChemAxon
Polarizability17.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
5-hydroxyindole acetaldehyde + L-Cysteine → 5-hydroxyindole thiazolidine carboxylate + Water
5-hydroxytryptophol + NAD+ → 5-hydroxyindole acetaldehyde + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • 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. [10644046 ]
Synthesis Reference: Marchand, B.; Streffer, Ch. Synthesis of 5-hydroxy-3-indolylacetaldehyde. Angew. Chem. (1959), 71 575.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
METABOLIGHTSMTBLC50157
HMDBHMDB04073
CHEMSPIDER67261
PUBCHEM74688
CHEBI50157
LIGAND-CPDC05634