ChemFOnt: Showing chemical card for N-Acetyl-5-methoxykynuramine (CFc000042909)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:40 UTC

Chemfont ID

CFc000042909

Molecule Identification

Common Name

N-Acetyl-5-methoxykynuramine

Definition

N-Acetyl-5-methoxykynuramine (AMK) is a melatonin metabolite. Its direct precursor, acetyl-N-formyl-5-methoxykynurenamine (AFMK), is a product of melatonin metabolization in the brain (PMID: 23963910 ). AMK is a potent scavenger of several reactive oxygen species (ROS) such as hydroxyl, peroxyl, and carbonate radicals as well as the non-radical singlet oxygen (PMID: 14599344 , 18643875 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N(gamma)-Acetyl-5-methoxykynurenamine	MeSH
N-Acetyl-5-methoxy kynurenamine	MeSH
N(1)-Acetyl-5-methoxykynuramine	MeSH
AMK kynuramine CPD	MeSH
AMKA	HMDB
N1-Acetyl-5-methoxykynuramine	HMDB
NSC 688265	HMDB
AMK	HMDB
K2	HMDB

Chemical Formula

C₁₂H₁₆N₂O₃

Average Molecular Weight

236.271

Monoisotopic Molecular Weight

236.116092383

IUPAC Name

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

Traditional Name

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

CAS Registry Number

52450-39-2

SMILES

COC1=CC=C(N)C(=C1)C(=O)CCNC(C)=O

InChI Identifier

InChI=1S/C12H16N2O3/c1-8(15)14-6-5-12(16)10-7-9(17-2)3-4-11(10)13/h3-4,7H,5-6,13H2,1-2H3,(H,14,15)

InChI Key

RJQIZOKNUKRKTP-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
Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Aniline or substituted anilines
Aryl alkyl ketone
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetamide
Vinylogous amide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-12023 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062497)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	0.4	ALOGPS
logP	0.33	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.22	ChemAxon
pKa (Strongest Basic)	3.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	65.13 m³·mol⁻¹	ChemAxon
Polarizability	25.3 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

HMDB0062497

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

390658

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetyl-5-methoxykynuramine (CFc000042909)

MOL for CFc000042909 (N-Acetyl-5-methoxykynuramine)

3D MOL for CFc000042909 (N-Acetyl-5-methoxykynuramine)

3D SDF for CFc000042909 (N-Acetyl-5-methoxykynuramine)

3D-SDF for CFc000042909 (N-Acetyl-5-methoxykynuramine)

PDB for CFc000042909 (N-Acetyl-5-methoxykynuramine)

3D PDB for CFc000042909 (N-Acetyl-5-methoxykynuramine)

SMILES for CFc000042909 (N-Acetyl-5-methoxykynuramine)

INCHI for CFc000042909 (N-Acetyl-5-methoxykynuramine)

Structure for CFc000042909 (N-Acetyl-5-methoxykynuramine)

3D Structure for CFc000042909 (N-Acetyl-5-methoxykynuramine)