ChemFOnt: Showing chemical card for Homocarnosine (CFc000000593)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:01 UTC

Chemfont ID

CFc000000593

Molecule Identification

Common Name

Homocarnosine

Definition

Homocarnosine is a normal human metabolite, the brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. (PMID 1266573 ). Increased concentration of CSF homocarnosine has been found in familial spastic paraplegia. (PMID 842287 ). Homocarnosinosis (an inherited disorder, OMIM 236130 ) is characterized by an elevated level of the dipeptide homocarnosine (Hca) in the Cerebrospinal fluid (CSF) and the brain and by carnosinuria and serum carnosinase deficiency, and can co-exist with paraplegia, retinitis pigmentosa, and a progressive mental deficiency. (PMID 3736769 ). In glial tumors of human brain the content of homocarnosine has been found to be lower than in brain tissue (PMID 1032224 ), while an increase in content of homocarnosine was observed in brain tissue of animals under experimental trauma of cranium. (PMID 1025883 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-Homocarnosine	ChEBI
(S)-Homocarnosine	ChEBI
gamma-Aminobutyryl-L-his	ChEBI
N-(4-Aminobutanoyl)-(S)-histidine	ChEBI
N-(4-Aminobutyryl)-L-histidine	ChEBI
N(alpha)-(4-Aminobutyryl)-L-histidine	ChEBI
L-Homocarnosine	Kegg
gamma-Aminobutyryl histidine	Kegg
N-(4-Amino-1-oxobutyryl)histidine	Kegg
g-Aminobutyryl-L-his	Generator
Γ-aminobutyryl-L-his	Generator
N(a)-(4-Aminobutyryl)-L-histidine	Generator
N(Α)-(4-aminobutyryl)-L-histidine	Generator
g-Aminobutyryl histidine	Generator
Γ-aminobutyryl histidine	Generator
gamma-Aminobutyryl-L-histidine	MeSH
Homocarnosine sulfate	MeSH
g-Aminobutyryl-L-histidine	HMDB
g-Aminobutyrylhistidine	HMDB
gamma-Aminobutyrylhistidine	HMDB
N-(4-Aminobutyryl)-histidine	HMDB

Chemical Formula

C₁₀H₁₆N₄O₃

Average Molecular Weight

240.259

Monoisotopic Molecular Weight

240.122240398

IUPAC Name

(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

Traditional Name

(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

CAS Registry Number

3650-73-5

SMILES

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

InChI Identifier

InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1

InChI Key

CCLQKVKJOGVQLU-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acyl-amine
Fatty amide
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Amino acid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Organooxygen compound
Primary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

L-histidine derivative (CHEBI:85981 )
N-acyl-L-alpha-amino acid (CHEBI:85981 )
homocarnosine (CHEBI:85981 )

Functional Ontology

Not Available

Brain (HMDB: HMDB0000745)
Prostate (HMDB: HMDB0000745)

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (HMDB: HMDB0000745)
Cerebrospinal fluid (HMDB: HMDB0000745)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Cellular substructure

Cytoplasm (HMDB: HMDB0000745)
Membrane (HMDB: HMDB0000745)

Source

Endogenous

Endogenous (HMDB: HMDB0000745)

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

Disease pathway

Homocarnosinosis (HMDB: HMDB0000745)
GABA-Transaminase Deficiency (HMDB: HMDB0000745)
Carnosinuria, Carnosinemia (HMDB: HMDB0000745)

Metabolic pathway

Inner Membrane Transport (PathBank: SMP0121270)

Role

Biological role

Metabolite (HMDB: HMDB0000745)
Metabolite (HMDB: HMDB0000745)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.37 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	9.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	59.75 m³·mol⁻¹	ChemAxon
Polarizability	24.49 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