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Showing Compound Acetyl-N-formyl-5-methoxykynurenamine (FDB023355)

Record Information
Version1.0
Creation date2011-09-21 00:28:35 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023355
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetyl-N-formyl-5-methoxykynurenamine
DescriptionAcetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration, with AFMK found in some patients exceeding the concentration of melatonin normally found in serum. (PMID: 16150112) [HMDB]
CAS Number52450-38-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamidehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H16N2O4
IUPAC nameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
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
Isomeric SMILESCOC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
Classification
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, GC-MS Spectrumsplash10-001i-1790000000-08a018599da99d325111Spectrum
GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, GC-MS Spectrumsplash10-004r-1941000000-1fd6a7b0aa4a93746dceSpectrum
GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, GC-MS Spectrumsplash10-001i-1790000000-08a018599da99d325111Spectrum
GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, GC-MS Spectrumsplash10-004r-1941000000-1fd6a7b0aa4a93746dceSpectrum
Predicted GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kfy-8790000000-29b99509d4ad702e0c17Spectrum
Predicted GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-N-formyl-5-methoxykynurenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01ri-0900000000-befc2619a8b03b67929f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0f79-1920000000-c1e957900fd03a5369422021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bl-0190000000-cc0a8bf1c63ec5bda44d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dl-2970000000-e59ea14239ec95d818892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-4900000000-87c88186c3d6cd7b6c512017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-0090000000-6ea3042b8fae674f87bb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-3490000000-f9119264a2c3c84527652017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9110000000-7e684511197690c0f5cb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1190000000-9ea054e52d4b2713e40a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9420000000-5c7a32c26de619ab85442021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9410000000-be01b9cb02bd8503009a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0170-0490000000-010747a672f5eb1374f02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bg-1950000000-b11b95cdcd40b6ee721a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kou-2900000000-ab1aed32a73b1f6ab74e2021-09-24View Spectrum
NMRNot Available
ChemSpider ID149637
ChEMBL IDCHEMBL1882218
KEGG Compound IDC05642
Pubchem Compound ID171161
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04259
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46183
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference