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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:19:52 UTC
Update Date2017-12-07 01:53:15 UTC
HMDB IDHMDB0004073
Secondary Accession Numbers
  • HMDB04073
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
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
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
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

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 Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.51 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      BiofluidStatusValueAgeSexConditionReferenceDetails
      FecesDetected but not Quantified Children (6 - 18 years old)Bothenthesitis-related arthritis details
      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 ID5-HYDROXYINDOLE_ACETALDEHYDE
      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 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

      General function:
      Involved in oxidoreductase activity
      Specific function:
      Not Available
      Gene Name:
      AOX1
      Uniprot ID:
      Q06278
      Molecular weight:
      147916.735
      Reactions
      5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
      Gene Name:
      MAOB
      Uniprot ID:
      P27338
      Molecular weight:
      58762.475
      Reactions
      Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
      Gene Name:
      MAOA
      Uniprot ID:
      P21397
      Molecular weight:
      59681.27
      Reactions
      Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
      Gene Name:
      ALDH9A1
      Uniprot ID:
      P49189
      Molecular weight:
      56291.485
      Reactions
      5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
      Gene Name:
      ALDH7A1
      Uniprot ID:
      P49419
      Molecular weight:
      58486.74
      Reactions
      5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
      Gene Name:
      ALDH1A3
      Uniprot ID:
      P47895
      Molecular weight:
      56107.995
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Not Available
      Gene Name:
      ALDH2
      Uniprot ID:
      P05091
      Molecular weight:
      56380.93
      Reactions
      5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
      Gene Name:
      ALDH3A2
      Uniprot ID:
      P51648
      Molecular weight:
      54847.36
      Reactions
      5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
      Gene Name:
      ALDH1B1
      Uniprot ID:
      P30837
      Molecular weight:
      57248.96
      Reactions
      5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
      General function:
      Involved in methyltransferase activity
      Specific function:
      Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
      Gene Name:
      INMT
      Uniprot ID:
      O95050
      Molecular weight:
      28833.695
      General function:
      Involved in protein methyltransferase activity
      Specific function:
      Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
      Gene Name:
      PRMT3
      Uniprot ID:
      O60678
      Molecular weight:
      59902.7