ChemFOnt: Showing chemical card for Acetyl-N-formyl-5-methoxykynurenamine (CFc000002109)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:54 UTC

Chemfont ID

CFc000002109

Molecule Identification

Common Name

Acetyl-N-formyl-5-methoxykynurenamine

Definition

Acetyl-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. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-N-formyl-5-methoxykynurenamine	HMDB
AFMK	HMDB
Formyl-N-acetyl-5-methoxykynurenamine	HMDB
N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide	HMDB
N1-Acetyl-N2-formyl-5-methoxykynurenine	HMDB
NSC 688263	HMDB
K1	HMDB

Chemical Formula

C₁₃H₁₆N₂O₄

Average Molecular Weight

264.2771

Monoisotopic Molecular Weight

264.11100701

IUPAC Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

Traditional Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

CAS Registry Number

52450-38-1

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 Key

JYWNYMJKURVPFH-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

kynurenamines (CHEBI:28613 )
a small molecule (CPD-12022 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Meningitis (HMDB: HMDB0004259)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12865098)
Cerebrospinal Fluid (CSF) (PMID: 16150112)
Cerebrospinal fluid (HMDB: HMDB0004259)

Excreta

Biofluid or Excreta

Feces (PMID: 26848182)

Cellular substructure

Cytoplasm (HMDB: HMDB0004259)

Source

Endogenous

Endogenous (HMDB: HMDB0004259)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004259)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.8 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023355

KNApSAcK ID

Not Available

Chemspider ID

149637

KEGG Compound ID

C05642

BioCyc ID

Not Available

BiGG ID

46183

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171161

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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.

Showing chemical card for Acetyl-N-formyl-5-methoxykynurenamine (CFc000002109)

MOL for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

3D MOL for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

3D SDF for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

3D-SDF for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

PDB for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

3D PDB for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

SMILES for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

INCHI for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

Structure for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)

3D Structure for CFc000002109 (Acetyl-N-formyl-5-methoxykynurenamine)