ChemFOnt: Showing chemical card for Carnosine (CFc000000023)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:37:10 UTC

Chemfont ID

CFc000000023

Molecule Identification

Common Name

Carnosine

Definition

Carnosine, which is also known as beta-alanyl-L-histidine) is a dipeptide consisting of the amino acids beta-alanine and histidine. It is found exclusively in animal tissues and is naturally produced in the body by the liver. Carnosine has a pKa value of 6.83, making it a good buffer for the pH range of animal muscles. Since beta-alanine is a non-proteogenic amino acid and is not incorporated into proteins, carnosine can be stored at relatively high concentrations (millimolar) in muscles, with concentrations as high as 17-25 mmol/kg (dry muscle). Carnosine is also highly concentrated in brain tissues. Carnosine has been shown to scavenge reactive oxygen species (ROS) as well as alpha-beta unsaturated aldehydes formed from peroxidation of fatty acids during oxidative stress. The antioxidant mechanism of carnosine is attributed to its chelating effect against divalent metal ions, superoxide dismutase (SOD)-like activity, as well as its ROS and free radicals scavenging ability (PMID: 16406688 ). Carnosine also buffers muscle cells, and acts as a neurotransmitter in the brain. Carnosine has the potential to suppress many of the biochemical changes that accompany ageing (e.g. protein oxidation, glycation, AGE formation, and cross-linking) and associated pathologies (PMID: 16804013 ). Some autistic patients take carnosine as a dietary supplement and attribute an improvement in their condition to it. Supplemental carnosine may increase corticosterone levels. This may explain the "hyperactivity" seen in autistic subjects at higher doses. A positive association between muscle tissue carnosine concentration and exercise performance has been found. beta-Alanine supplementation is thought increase exercise performance by promoting carnosine production in muscle. Exercise has conversely been found to increase muscle carnosine concentrations, and muscle carnosine content is higher in athletes engaging in anaerobic exercise. Carnosine is also a biomarker for the consumption of meat. Elevated levels of urinary and plasma carnosine are associated with carnosinuria (also known as carnosinemia), which is an inborn error of metabolism. caused by a deficiency of the enzyme carnosinase. Carnosinas cleaves carnosine into its constituent amino acids: beta-Alanine and histidine. Carnonsinemia results in an excess of carnosine in the urine, cerebrospinal fluid, blood, and nervous tissue. A variety of neurological symptoms have been associated with carnosinemia. They include: hypotonia, developmental delay, mental retardation, degeneration of axons, sensory neuropathy, tremors, demyelinization, gray matter anomalies, myoclonic seizures, and loss of purkinje fibers.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ribonuclease, pancreatic	MeSH
RNase a	MeSH
Ribonuclease I	MeSH
Ribonuclease a	MeSH
Ribonuclease (pancreatic)	MeSH
RNase I	MeSH
Pancreatic rnase	MeSH
Pancreatic ribonuclease	MeSH
RNase, pancreatic	MeSH

Chemical Formula

C₉H₁₄N₄O₃

Average Molecular Weight

226.2325

Monoisotopic Molecular Weight

226.106590334

IUPAC Name

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

Traditional Name

2-[(3-amino-1-hydroxypropylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

305-84-0

SMILES

NCCC(O)=NC(CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)

InChI Key

CQOVPNPJLQNMDC-UHFFFAOYSA-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
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Primary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Primary aliphatic amine
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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: 17031479)
Saliva (HMDB: HMDB0000033)

Organ

Cell

Fibroblasts (HMDB: HMDB0000033)
Neuron (HMDB: HMDB0000033)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000033)

Excreta

Biofluid or Excreta

Urine (PMID: 9029640)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000033)
Membrane (HMDB: HMDB0000033)

Tissue substructure

Muscle (HMDB: HMDB0000033)

Source

Exogenous

Exogenous (HMDB: HMDB0000033)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Oat (FooDB: FOOD00022)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Root vegetable

Carrot (FooDB: FOOD00245)
Parsnip (FooDB: FOOD00129)

Leaf vegetable

Swiss chard (FooDB: FOOD00237)

Fruit vegetable

Herb and spice

Herb

Dill (FooDB: FOOD00013)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Gourd

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Endogenous

Endogenous (HMDB: HMDB0000033)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (HMDB: HMDB0000033)
Beta-Alanine metabolism (HMDB: HMDB0000033)

Disease pathway

Carnosinuria, Carnosinemia (HMDB: HMDB0000033)
GABA-Transaminase Deficiency (PathBank: SMP0120478)
Histidinemia (PathBank: SMP0120493)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.44 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.08 m³·mol⁻¹	ChemAxon
Polarizability	22.25 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

HMDB0259615

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005612

KNApSAcK ID

Not Available

Chemspider ID

9001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phosphoglucomutase

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Vezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6

Showing chemical card for Carnosine (CFc000000023)

MOL for CFc000000023 (Carnosine)

3D MOL for CFc000000023 (Carnosine)

3D SDF for CFc000000023 (Carnosine)

3D-SDF for CFc000000023 (Carnosine)

PDB for CFc000000023 (Carnosine)

3D PDB for CFc000000023 (Carnosine)

SMILES for CFc000000023 (Carnosine)

INCHI for CFc000000023 (Carnosine)

Structure for CFc000000023 (Carnosine)

3D Structure for CFc000000023 (Carnosine)