ChemFOnt: Showing chemical card for 2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid (CFc000136169)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 22:09:33 UTC

Chemfont ID

CFc000136169

Molecule Identification

Common Name

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

Definition

3-Methylhistidine 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. 3-Methylhistidine is a very strong basic compound (based on its pKa). 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. A L-histidine derivative that is L-histidine substituted by a methyl group at position 3 on the imidazole ring.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid	ChEBI
3-Methyl-L-histidine	ChEBI
N-pros-Methyl-L-histidine	ChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoate	Generator
3-N-Methyl-L-histidine	HMDB
L-3-Methylhistidine	HMDB
N(pros)-Methyl-L-histidine	HMDB
N3-Methyl-L-histidine	HMDB
3-Methylhistidine hydride	HMDB
3-Methylhistidine dihydrochloride	HMDB
3-Methylhistidine	ChEBI
Pi methylhistidine	HMDB
N(Pi)-methylhistidine	HMDB
N Pi-methylhistidine	HMDB

Chemical Formula

C₇H₁₁N₃O₂

Average Molecular Weight

169.1811

Monoisotopic Molecular Weight

169.085126611

IUPAC Name

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

Traditional Name

3,methylhistidine

CAS Registry Number

368-16-1

SMILES

[H][C@](N)(CC1=CN=CN1C)C(O)=O

InChI Identifier

InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1

InChI Key

JDHILDINMRGULE-LURJTMIESA-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
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:27596 )
L-histidine derivative (CHEBI:27596 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.93 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.96 m³·mol⁻¹	ChemAxon
Polarizability	16.58 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