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Record Information
Version4.0
Creation Date2009-07-25 00:10:24 UTC
Update Date2017-09-27 08:27:10 UTC
HMDB IDHMDB0012948
Secondary Accession Numbers
  • HMDB12948
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
ValueSource
3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindoleChEBI
6-HydroxymelatoninChEBI
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 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
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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 Area92.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.87 m³·mol⁻¹ChemAxon
Polarizability20.94 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-001i-8900000000-a7dfb341fd862129e334View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-4920000000-d09c34c768fad3b989b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06sl-0930000000-9db8e3dae4d6b087e5b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ec-1900000000-218e623c24db925a83c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-3900000000-36941f33d52e98b5147aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0980000000-ca7dd839f42d8cd4bea9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-6d5837bfc6681842fbb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-6900000000-a30b799e2dc97afbd9b3View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Displaying 1 entry
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
METLIN IDNot Available
PubChem Compound440743
PDB IDNot Available
ChEBI ID28736
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