Showing metabocard for Acetyl-N-formyl-5-methoxykynurenamine (BMDB0004259)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:57 UTC
Update Date2020-05-21 16:28:51 UTC
BMDB IDBMDB0004259
Secondary Accession Numbers
  • BMDB04259
Metabolite Identification
Common NameAcetyl-N-formyl-5-methoxykynurenamine
DescriptionAcetyl-N-formyl-5-methoxykynurenamine, also known as acetyl-n-formyl-5-methoxykynurenamine, 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. Acetyl-N-formyl-5-methoxykynurenamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Acetyl-N-formyl-5-methoxykynurenamine exists in all living organisms, ranging from bacteria to humans. Acetyl-N-formyl-5-methoxykynurenamine can be biosynthesized from melatonin; which is catalyzed by the enzyme indoleamine 2,3-dioxygenase 1. In cattle, acetyl-N-formyl-5-methoxykynurenamine is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-N-formyl-5-methoxykynurenamineHMDB
AFMKHMDB
Formyl-N-acetyl-5-methoxykynurenamineHMDB
N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamideHMDB
N1-Acetyl-N2-formyl-5-methoxykynurenineHMDB
NSC 688263HMDB
K1HMDB
Chemical FormulaC13H16N2O4
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
IUPAC NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
Traditional NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
CAS Registry Number52450-38-1
SMILES
COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
InChI Identifier
InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)
InChI KeyJYWNYMJKURVPFH-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
  • Methoxyaniline
  • Anilide
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • N-arylamide
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetamide
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.158Not Available
Predicted Properties
PropertyValueSource
logP0.5ALOGPS
logP0.34ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.8 m³·mol⁻¹ChemAxon
Polarizability27.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d325111View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d325111View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfy-8790000000-29b99509d4ad702e0c17View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01ri-0900000000-befc2619a8b03b67929fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0f79-1920000000-c1e957900fd03a536942View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bl-0190000000-cc0a8bf1c63ec5bda44dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dl-2970000000-e59ea14239ec95d81889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-4900000000-87c88186c3d6cd7b6c51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-0090000000-6ea3042b8fae674f87bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-3490000000-f9119264a2c3c8452765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9110000000-7e684511197690c0f5cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1190000000-9ea054e52d4b2713e40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9420000000-5c7a32c26de619ab8544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9410000000-be01b9cb02bd8503009aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0170-0490000000-010747a672f5eb1374f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bg-1950000000-b11b95cdcd40b6ee721aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kou-2900000000-ab1aed32a73b1f6ab74eView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004259
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023355
KNApSAcK IDNot Available
Chemspider ID149637
KEGG Compound IDC05642
BioCyc IDNot Available
BiGG ID46183
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound171161
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis Referencede Almeida Eduardo A; Martinez Glaucia R; Klitzke Clecio F; de Medeiros Marisa H G; Di Mascio Paolo Oxidation of melatonin by singlet molecular oxygen (O2(1deltag)) produces N1-acetyl-N2-formyl-5-methoxykynurenine. Journal of pineal research (2003), 35(2), 131-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Indoleamine 2,3-dioxygenase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
IDO1
Uniprot ID:
F1N7C5
Molecular weight:
50061.0
Reactions
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails