ChemFOnt: Showing chemical card for N-Acetyl-3-methylhistidine (CFc000220604)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:49 UTC

Chemfont ID

CFc000220604

Molecule Identification

Common Name

N-Acetyl-3-methylhistidine

Definition

N-Acetyl-3-methylhistidine, an N-acetyl-L-amino acid, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing histidine or a derivative thereof resulting from a reaction of histidine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetyl-3-methylhistidine is an acetylated derivative of 3-methylhistidine and a very strong basic compound (based on its pKa). N-Acetyl-3-methylhistidine has been found to be associated with prostate cancer (PMID: 28423352 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Acetamido-3-(1-methyl-1H-imidazol-5-yl)propanoic acid	HMDB
(2S)-2-Acetamido-3-(1-methyl-1H-imidazol-5-yl)propionic acid	HMDB
N-Acetyl-3-methyl-L-histidine	HMDB
N-Acetyl-L-3-methylhistidine	HMDB
N-Acetyl-3-methylhistidine	HMDB

Chemical Formula

C₉H₁₃N₃O₃

Average Molecular Weight

211.221

Monoisotopic Molecular Weight

211.095691291

IUPAC Name

(2S)-2-acetamido-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-acetamido-3-(3-methylimidazol-4-yl)propanoic acid

CAS Registry Number

37841-04-6

SMILES

CN1C=NC=C1C[C@H](NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C9H13N3O3/c1-6(13)11-8(9(14)15)3-7-4-10-5-12(7)2/h4-5,8H,3H2,1-2H3,(H,11,13)(H,14,15)/t8-/m0/s1

InChI Key

FKTXRTPBUWLETL-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Imidazolyl carboxylic acid derivative
N-substituted imidazole
Azole
Imidazole
Acetamide
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26317986)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Source

Exogenous

Exogenous (HMDB: HMDB0240341)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.51 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	-2.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.4 m³·mol⁻¹	ChemAxon
Polarizability	20.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240341

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

167717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193270

PDB ID

Not Available

ChEBI ID

133183

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetyl-3-methylhistidine (CFc000220604)

MOL for CFc000220604 (N-Acetyl-3-methylhistidine)

3D MOL for CFc000220604 (N-Acetyl-3-methylhistidine)

3D SDF for CFc000220604 (N-Acetyl-3-methylhistidine)

3D-SDF for CFc000220604 (N-Acetyl-3-methylhistidine)

PDB for CFc000220604 (N-Acetyl-3-methylhistidine)

3D PDB for CFc000220604 (N-Acetyl-3-methylhistidine)

SMILES for CFc000220604 (N-Acetyl-3-methylhistidine)

INCHI for CFc000220604 (N-Acetyl-3-methylhistidine)

Structure for CFc000220604 (N-Acetyl-3-methylhistidine)

3D Structure for CFc000220604 (N-Acetyl-3-methylhistidine)