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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:24 UTC
Update Date2023-02-21 17:17:52 UTC
HMDB IDHMDB0012948
Secondary Accession Numbers
  • HMDB12948
Metabolite Identification
Common NameFormyl-5-hydroxykynurenamine
DescriptionFormyl-5-hydroxykynurenamine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group and a phenyl group. Formyl-5-hydroxykynurenamine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Formyl-5-hydroxykynurenamine can be biosynthesized from serotonin; which is mediated by the enzyme indoleamine 2,3-dioxygenase 1 [EC 1.13.11.52]. In humans, formyl-5-hydroxykynurenamine is involved in the tryptophan metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindoleChEBI
N-(2(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamideChEBI
N-(2-(6-Hydroxy-5-methoxyindol-3-yl)ethyl)-acetamideChEBI
N-(2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)-acetamideHMDB
N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]-acetamideHMDB
N-[2-(6-Hydroxy-5-methoxyindol-3-yl)ethyl]-acetamideHMDB
Chemical FormulaC10H12N2O3
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
IUPAC NameN-[2-(3-aminopropanoyl)-4-hydroxyphenyl]formamide
Traditional NameN-[2-(3-aminopropanoyl)-4-hydroxyphenyl]formamide
CAS Registry Number958733-17-0
SMILES
NCCC(=O)C1=C(NC=O)C=CC(O)=C1
InChI Identifier
InChI=1S/C10H12N2O3/c11-4-3-10(15)8-5-7(14)1-2-9(8)12-6-13/h1-2,5-6,14H,3-4,11H2,(H,12,13)
InChI KeyCKAXPTWYSHDIBN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Anilide
  • Benzoyl
  • Aryl alkyl ketone
  • N-arylamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Benzenoid
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029224
KNApSAcK IDNot Available
Chemspider ID389614
KEGG Compound IDC05647
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440743
PDB IDNot Available
ChEBI ID28736
Food Biomarker OntologyNot Available
VMH IDF5HOXKYN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Frisch H, Waldhauser F, Waldhor T, Mullner-Eidenbock A, Neupane P, Schweitzer K: Increase in 6-hydroxymelatonin excretion in humans during ascent to high altitudes. J Clin Endocrinol Metab. 2004 Sep;89(9):4388-90. [PubMed:15356035 ]

Enzymes

General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
Serotonin + Oxygen → Formyl-5-hydroxykynurenaminedetails
General function:
Involved in heme binding
Specific function:
Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Molecular weight:
47074.745
Reactions
Serotonin + Oxygen → Formyl-5-hydroxykynurenaminedetails