ChemFOnt: Showing chemical card for 2-amino-3-(1H-imidazol-5-yl)propanoic acid (CFc000135296)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 22:08:09 UTC

Chemfont ID

CFc000135296

Molecule Identification

Common Name

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

Definition

L-Histidine, also known as H, 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. L-Histidine is a very strong basic compound (based on its pKa). L-Histidine exists in all living species, ranging from bacteria to humans. In humans, L-histidine is involved in methylhistidine metabolism. L-Histidine is a potentially toxic compound. L-Histidine, with regard to humans, has been found to be associated with several diseases such as lewy body disease, schizophrenia, eosinophilic esophagitis, and colorectal cancer; L-histidine has also been linked to the inborn metabolic disorder propionic acidemia. The L-enantiomer of the amino acid histidine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-4-(2-Amino-2-carboxyethyl)imidazole	ChEBI
(S)-alpha-Amino-1H-imidazole-4-propanoic acid	ChEBI
(S)-alpha-Amino-1H-imidazole-4-propionic acid	ChEBI
H	ChEBI
His	ChEBI
HISTIDINE	ChEBI
L-(-)-Histidine	ChEBI
L-Histidin	ChEBI
(S)-a-Amino-1H-imidazole-4-propanoate	Generator
(S)-a-Amino-1H-imidazole-4-propanoic acid	Generator
(S)-alpha-Amino-1H-imidazole-4-propanoate	Generator
(S)-Α-amino-1H-imidazole-4-propanoate	Generator
(S)-Α-amino-1H-imidazole-4-propanoic acid	Generator
(S)-a-Amino-1H-imidazole-4-propionate	Generator
(S)-a-Amino-1H-imidazole-4-propionic acid	Generator
(S)-alpha-Amino-1H-imidazole-4-propionate	Generator
(S)-Α-amino-1H-imidazole-4-propionate	Generator
(S)-Α-amino-1H-imidazole-4-propionic acid	Generator
(S)-1H-Imidazole-4-alanine	HMDB
(S)-2-Amino-3-(4-imidazolyl)propionsaeure	HMDB
(S)-Histidine	HMDB
(S)1H-Imidazole-4-alanine	HMDB
3-(1H-Imidazol-4-yl)-L-alanine	HMDB
Amino-1H-imidazole-4-propanoate	HMDB
Amino-1H-imidazole-4-propanoic acid	HMDB
Amino-4-imidazoleproprionate	HMDB
Amino-4-imidazoleproprionic acid	HMDB
Glyoxaline-5-alanine	HMDB
Histidine, L isomer	HMDB
Histidine, L-isomer	HMDB
L-Isomer histidine	HMDB
L-Histidine	KEGG

Chemical Formula

C₆H₉N₃O₂

Average Molecular Weight

155.1546

Monoisotopic Molecular Weight

155.069476547

IUPAC Name

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

Traditional Name

L-histidine

CAS Registry Number

71-00-1

SMILES

N[C@@H](CC1=CNC=N1)C(O)=O

InChI Identifier

InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

InChI Key

HNDVDQJCIGZPNO-YFKPBYRVSA-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
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organooxygen compound
Organonitrogen 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

proteinogenic amino acid (CHEBI:15971 )
L-alpha-amino acid (CHEBI:15971 )
histidine (CHEBI:15971 )
Common amino acids (C00135 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	71.3 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.6	ChemAxon
logS	-0.34	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.06 m³·mol⁻¹	ChemAxon
Polarizability	14.67 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