Np mrd loader

Record Information
Version1.0
Created at2022-05-11 16:42:02 UTC
Updated at2022-05-11 16:42:02 UTC
NP-MRD IDNP0087168
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetyl-N-formyl-5-methoxykynurenamine
DescriptionAcetyl-N-formyl-5-methoxykynurenamine, also known as AFMK or NSC 688263, 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 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 through the action of the enzyme indoleamine 2,3-dioxygenase 1. It was first documented in 2005 (PMID: 16150112). In humans, acetyl-N-formyl-5-methoxykynurenamine is involved in tryptophan metabolism.
Structure
Thumb
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 Mass264.2771 Da
Monoisotopic Mass264.11101 Da
IUPAC NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
Traditional NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004259
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1111/j.1600-079X.2005.00247.x. [PubMed:16150112 ]