Acetyl-N-formyl-5-methoxykynurenamine (CHEM035668)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:58:26 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035668
Identification
Common NameAcetyl-N-formyl-5-methoxykynurenamine
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass264.277 g/mol
Monoisotopic Mass264.111 g/mol
CAS Registry Number52450-38-1
IUPAC NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
Traditional NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
SMILESCOC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d325111Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dceSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d325111Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfy-8790000000-29b99509d4ad702e0c17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01ri-0900000000-befc2619a8b03b67929fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0f79-1920000000-c1e957900fd03a536942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bl-0190000000-cc0a8bf1c63ec5bda44dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dl-2970000000-e59ea14239ec95d81889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-4900000000-87c88186c3d6cd7b6c51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-0090000000-6ea3042b8fae674f87bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-3490000000-f9119264a2c3c8452765Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9110000000-7e684511197690c0f5cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1190000000-9ea054e52d4b2713e40aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9420000000-5c7a32c26de619ab8544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9410000000-be01b9cb02bd8503009aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0170-0490000000-010747a672f5eb1374f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bg-1950000000-b11b95cdcd40b6ee721aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kou-2900000000-ab1aed32a73b1f6ab74eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004259
FooDB IDFDB023355
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46183
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID149637
ChEBI IDNot Available
PubChem Compound ID171161
Kegg Compound IDC05642
YMDB IDNot Available
ECMDB IDM2MDB005840
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. de 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.
2. de 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.
3. Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6.