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Record Information
Version3.6
Creation Date2006-08-13 15:27:56 UTC
Update Date2016-02-11 01:06:42 UTC
HMDB IDHMDB04259
Secondary Accession NumbersNone
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
ValueSource
N-Acetyl-N-formyl-5-methoxykynuramineMetaCyc
AFMKMetaCyc
Formyl-N-acetyl-5-methoxykynurenamineMetaCyc
N-Acetyl-N-formyl-5-methoxykynurenamineMetaCyc
N-[3-(2-formamido-5-Methoxy-phenyl)-3-oxo-propyl]acetamideHMDB
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 KeyInChIKey=JYWNYMJKURVPFH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Methoxyaniline
  • Acetophenone
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Beta-aminoketone
  • Acetamide
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Ketone
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and 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
Water Solubility0.17 mg/mLALOGPS
logP0.5ALOGPS
logP0.34ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.5 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.8 m3·mol-1ChemAxon
Polarizability27.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000065 (0.000059-0.00189) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.28 (0.06-0.50) uMAdult (>18 years old)Not Specified
Meningitis
details
Associated Disorders and Diseases
Disease References
Meningitis
  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. [16150112 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023355
KNApSAcK IDNot Available
Chemspider ID149637
KEGG Compound IDC05642
BioCyc IDNot Available
BiGG ID46183
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04259
Metagene LinkHMDB04259
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)Download (PDF)
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. [16150112 ]

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
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails
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
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails