Showing metabocard for 5-Hydroxyindoleacetaldehyde (BMDB0004073)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:38 UTC
Update Date2020-05-21 16:28:51 UTC
BMDB IDBMDB0004073
Secondary Accession Numbers
  • BMDB04073
Metabolite Identification
Common Name5-Hydroxyindoleacetaldehyde
Description5-5-5-hydroxyindoleacetaldehyde, also known as 5-5-hydroxyindoleacetaldehyde, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5-5-5-hydroxyindoleacetaldehyde is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5-5-5-hydroxyindoleacetaldehyde participates in a number of enzymatic reactions, within cattle. In particular, 5-5-5-hydroxyindoleacetaldehyde can be biosynthesized from serotonin through the action of the enzyme kynurenine 3-monooxygenase. In addition, 5-5-5-hydroxyindoleacetaldehyde can be converted into 5-hydroxyindoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In cattle, 5-5-hydroxyindoleacetaldehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-HialChEBI
5-Hydroxyindole-3-acetaldehydeChEBI
(5-Hydroxy-1H-indol-3-yl)acetaldehydeHMDB
(5-Hydroxyindol-3-yl)acetaldehydeHMDB
5-Hydroxy-1H-indole-3-acetaldehydeHMDB
HydroxyindoleacetaldehydeHMDB
5-HydroxytryptaldehydeHMDB
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
Traditional Namehydroxyindoleacetaldehyde
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
Description belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
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
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.51 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-0900000000-82ea66debc45b5a54912View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-4590000000-148aa38d23d73f5990a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-34afefea4e019e029852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057j-0900000000-c324c5351368276b781eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ng-2900000000-b5cae8ea903e8b80ef0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-f492ed9bb605e0b7b03bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-9fb25b933c4987b62deeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-0c78360f8596defdda87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-8c82c2093e14f3857e5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0900000000-6c3085f4067426eeb1f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-1900000000-fc0d25838e197398d090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ce155c63a4e18d180895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-0900000000-3967b0a653903263d918View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-b3f6f7944533b77bfd8bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004073
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030573
KNApSAcK IDNot Available
Chemspider ID67261
KEGG Compound IDC05634
BioCyc IDNot Available
BiGG ID46165
Wikipedia LinkNot Available
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Aldehyde oxidase 1
General function:
Nucleotide transport and metabolism
Specific function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:
AOX1
Uniprot ID:
P48034
Molecular weight:
147611.0
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
Enzyme Details
2. Aldehyde dehydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P20000
Molecular weight:
56653.0
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + NADHdetails
Enzyme Details
3. Kynurenine 3-monooxygenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
KMO
Uniprot ID:
E1BN59
Molecular weight:
51032.0
Reactions
Serotonin + NADPH + Oxygen → 5-Hydroxyindoleacetaldehyde + NADP + Waterdetails