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Record Information
Version4.0
Creation Date2006-08-13 10:34:42 UTC
Update Date2017-09-27 08:24:26 UTC
HMDB IDHMDB0004086
Secondary Accession Numbers
  • HMDB04086
Metabolite Identification
Common Name5-Hydroxy-N-formylkynurenine
Description5-Hydroxy-N-formylkynurenine is an intermediate in tryptophan metabolism. 5-Hydroxy-N-formylkynurenine is converted from 5-Hydroxy-L-tryptophan via the enzyme, indoleamine 2,3-dioxygenase [EC:1.13.11.52].
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H12N2O5
Average Molecular Weight252.2234
Monoisotopic Molecular Weight252.074621504
IUPAC Name2-amino-4-(2-formamido-5-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name5-hydroxy-N-formylkynurenine
CAS Registry NumberNot Available
SMILES
NC(CC(=O)C1=C(NC=O)C=CC(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C11H12N2O5/c12-8(11(17)18)4-10(16)7-3-6(15)1-2-9(7)13-5-14/h1-3,5,8,15H,4,12H2,(H,13,14)(H,17,18)
InChI KeyLSTOUSIIVKMJBU-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
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Anilide
  • Benzoyl
  • Gamma-keto acid
  • Aryl alkyl ketone
  • N-arylamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Vinylogous amide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Primary amine
  • Primary aliphatic 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
LogP-2.532Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP-2ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.7 m³·mol⁻¹ChemAxon
Polarizability23.39 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, Positivesplash10-03g3-6930000000-3311b36474c1596a6950View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-6943000000-3f2c0afb26906107faceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0290000000-b437a74ea548372439c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-072i-2930000000-61aaa4ae433646bdf721View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ri-1900000000-a7d341b29c5f6b98ce5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0090000000-9263dc7987252b280720View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5490000000-71350a32f06522a0c07aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9610000000-0edca97527513a85e26eView 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 IDFDB023307
KNApSAcK IDNot Available
Chemspider ID389615
KEGG Compound IDC05648
BioCyc IDNot Available
BiGG ID46195
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440744
PDB IDNot Available
ChEBI ID2065
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
Oxitriptan + Oxygen → 5-Hydroxy-N-formylkynureninedetails
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5
Reactions
5-Hydroxy-N-formylkynurenine + Water → 5-Hydroxykynurenine + Formic aciddetails
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
Oxitriptan + Oxygen → 5-Hydroxy-N-formylkynureninedetails