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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Hydroxyindoleacetaldehyde (HMDB04073)

Record Information
Version 3.5
Creation Date 2006-08-13 04:19:52 -0600
Update Date 2013-02-08 17:12:58 -0700
HMDB ID HMDB04073
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Hydroxyindoleacetaldehyde
Description 5-Hydroxyindoleacetaldehyde is a biogenic aldehyde of serotonin derived from the action of monoamine oxidase (MAO). (PMIDs 11306106, 2470392).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H9NO2
Average Molecular Weight 175.184
Monoisotopic Molecular Weight 175.063328537
IUPAC Name 2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
Traditional IUPAC Name 2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
CAS Registry Number 1892-21-3
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 Key OBFAPCIUSYHFIE-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class N/A
Other Descriptors
  • a small molecule(Cyc)
  • hydroxyindole(ChEBI)
  • indoleacetaldehyde(ChEBI)
Substituents
  • Aldehyde
  • Phenol
  • Phenol Derivative
  • Pyrrole
Direct Parent Indoles
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.32 g/L ALOGPS
LogP 1.93 ALOGPS
LogP 1.25 ChemAxon
LogS -2.12 ALOGPS
pKa (strongest acidic) 9.55 ChemAxon
pKa (strongest basic) -5.5 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 53.09 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 49.51 ChemAxon
Polarizability 17.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023299
KNApSAcK ID Not Available
Chemspider ID 67261 Link_out
KEGG Compound ID C05634 Link_out
BioCyc ID Not Available
BiGG ID 46165 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB04073 Link_out
Metagene Link HMDB04073 Link_out
METLIN ID Not Available
PubChem Compound 74688 Link_out
PDB ID Not Available
ChEBI ID 50157 Link_out
References
Synthesis Reference Marchand, B.; Streffer, Ch. Synthesis of 5-hydroxy-3-indolylacetaldehyde. Angew. Chem. (1959), 71 575.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Aldehyde oxidase
Reactions:
  • an aldehyde + H2O + O2 = a carboxylic acid + H2O2 [RN:R00635]
Gene Name: AOX1
Uniprot ID: Q06278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] B
Reactions:
  • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
  • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
  • 4-trimethylammoniobutanal + NAD+ + H2O = 4-trimethylammoniobutanoate + NADH + 2 H+ [RN:R03283]
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
  • L-2-aminoadipate 6-semialdehyde + NAD(P)+ + H2O = L-2-aminoadipate + NAD(P)H + H+ [RN:R03102 R03103]
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions:
  • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Indolethylamine N-methyltransferase
Reactions:
  • S-adenosyl-L-methionine + an amine = S-adenosyl-L-homocysteine + a methylated amine [RN:R02808]
Gene Name: INMT
Uniprot ID: O95050 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein arginine N-methyltransferase 3
Reactions:
    Gene Name: PRMT3
    Uniprot ID: O60678 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA