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Record Information
Version1.0
Creation Date2016-09-30 22:18:44 UTC
Update Date2020-06-04 21:54:05 UTC
BMDB IDBMDB0000033
Secondary Accession Numbers
  • BMDB00033
Metabolite Identification
Common NameCarnosine
DescriptionCarnosine, also known as b-alanylhistidine or ignotine, 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. Carnosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Carnosine exists in all living species, ranging from bacteria to humans. Carnosine is a potentially toxic compound. Carnosine has been found to be associated with several diseases known as eosinophilic esophagitis, crohn's disease, ulcerative colitis, and alzheimer's disease; also carnosine has been linked to the inborn metabolic disorders including carnosinuria.
Structure
Thumb
Synonyms
ValueSource
Nalpha-(beta-alanyl)-L-histidineChEBI
Nalpha-(b-alanyl)-L-histidineGenerator
Nalpha-(β-alanyl)-L-histidineGenerator
b-Alanyl-L-histidineHMDB
b-AlanylhistidineHMDB
beta-Alanyl-L-histidineHMDB
beta-AlanylhistidineHMDB
IgnotineHMDB
KarnozinHMDB
KarnozznHMDB
L-CarnosineHMDB
N-(3-Aminopropanoyl)histidineHMDB
N-(b-Alanyl)-L-histidineHMDB
N-b-Alanyl-L-histidineHMDB
N-beta-Alanyl-L-histidineHMDB
SevitinHMDB
Carnosine, (D-his)-isomerHMDB
Hydrochloride, carnosineHMDB
L CarnosineHMDB
Carnosine hydrochlorideHMDB
beta AlanylhistidineHMDB
Chemical FormulaC9H14N4O3
Average Molecular Weight226.2325
Monoisotopic Molecular Weight226.106590334
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number305-84-0
SMILESNot Available
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)/t7-/m0/s1
InChI KeyCQOVPNPJLQNMDC-ZETCQYMHSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid 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
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point253 - 256 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility384 mg/mLNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Brain
  • Colostrum
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Muscle
  • Neuron
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30 +/- 12 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected and Quantified15-20 uMNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified393 +/- 130 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified22085 +/- 4859 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected and Quantified0.48 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.50 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.46 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.46 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1802.96 +/- 87.68 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified2187.41 +/- 125.15 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified89360 +/- 4060 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified4730 +/- 480 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified2492.74 +/- 320.38 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified3960 +/- 640 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified4460 +/- 430 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified3447.54 +/- 171.14 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1715-3619 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified9900 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified433-701 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified9690-13658 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified0.47 +/- 0.24 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified0.47 +/- 0.24 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Semimembranosus MuscleDetected and Quantified21958 +/- 3048 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified12 +/- 3 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Fed pasture vs barley-based concentrate
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Fed pasture vs barley-based concentrate
details
HMDB IDHMDB0000033
DrugBank IDDB11695
Phenol Explorer Compound IDNot Available
FooDB IDFDB012937
KNApSAcK IDNot Available
Chemspider ID388363
KEGG Compound IDC00386
BioCyc IDCARNOSINE
BiGG ID1800369
Wikipedia LinkCarnosine
METLIN ID38
PubChem Compound439224
PDB IDNot Available
ChEBI ID15727
References
Synthesis ReferenceVezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:
CNDP2
Uniprot ID:
Q3ZC84
Molecular weight:
52655.0
Reactions
Carnosine + Water → Beta-Alanine + L-Histidinedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
A5PJL9
Molecular weight:
54461.0
Reactions
Adenosine triphosphate + L-Histidine + Beta-Alanine → ADP + Hydrogen phosphate + Carnosinedetails