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Record Information
Version3.6
Creation Date2009-07-25 00:10:24 UTC
Update Date2013-02-09 00:29:34 UTC
HMDB IDHMDB12948
Secondary Accession NumbersNone
Metabolite Identification
Common NameFormyl-5-hydroxykynurenamine
DescriptionFormyl-5-hydroxykynurenamine is found in the tryptophan metabolism pathway. It is produced from serotonin through the action of indoleamine 2,3-dioxygenase [EC:1.13.11.52].
Structure
Thumb
Synonyms
  1. 3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole
  2. 6-Hydroxymelatonin
  3. N-(2(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamide
  4. N-(2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)-Acetamide
  5. N-(2-(6-Hydroxy-5-methoxyindol-3-yl)ethyl)-Acetamide
  6. N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]-Acetamide
  7. N-[2-(6-Hydroxy-5-methoxyindol-3-yl)ethyl]-Acetamide
Chemical FormulaC10H12N2O3
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
IUPAC NameN-[2-(3-aminopropanoyl)-4-hydroxyphenyl]formamide
Traditional IUPAC NameN-[2-(3-aminopropanoyl)-4-hydroxyphenyl]formamide
CAS Registry Number2208-41-5
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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassAminobenzoic Acid Derivatives
Other Descriptors
  • Acetophenones
  • Organic Compounds
Substituents
  • Aminophenol Derivative
  • Benzoyl
  • Beta Aminoketone
  • Ketone
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
Direct ParentAminobenzoic Acid Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 solubility2.48 g/LALOGPS
logP-0.38ALOGPS
logP-0.41ChemAxon
logS-1.9ALOGPS
pKa (strongest acidic)8.85ChemAxon
pKa (strongest basic)9.61ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area92.42ChemAxon
rotatable bond count4ChemAxon
refractivity56.87ChemAxon
polarizability20.94ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029224
KNApSAcK IDNot Available
Chemspider ID389614
KEGG Compound IDC05647
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12948
Metagene LinkHMDB12948
METLIN IDNot Available
PubChem Compound440743
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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