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Bovine Metabolome Database



Showing metabocard for Carnosine (BMDB00033)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-30 15:15:26
Accession Number BMDB00033
Common Name Carnosine
Description Carnosine (beta-alanyl-L-histidine) is found exclusively in animal tissues. It is a dipeptide of the amino acids beta-alanine and histidine. Carnosine has the potential to suppress many of the biochemical changes (e.g., protein oxidation, glycation, AGE formation, and cross-linking) that accompany aging and associated pathologies (PMID 16804013). It is highly concentrated in muscle and brain tissues. Some autistics patients take it 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. Carnosine also exhibits some antioxidant effects. The antioxidant mechanism of carnosine is attributed to its chelating effect against metal ions, superoxide dismutase (SOD)-like activity, ROS and free radicals scavenging ability (PMID 16406688)
Synonyms
  1. Beta-Alanyl-L-histidine
  2. Carnosine
  3. Ignotine
  4. Karnozin
  5. Karnozzn
  6. L-Carnosine
  7. N-(3-Aminopropanoyl)histidine
  8. N-(b-Alanyl)-L-histidine
  9. N-b-alanyl-L-Histidine
  10. N-beta-alanyl-L-Histidine
  11. b-Alanyl-L-histidine
  12. b-Alanylhistidine
  13. beta-Alanylhistidine
  14. Sevitin
Chemical IUPAC Name (2S)-2-(3-aminopropanoylamino)-3-(3H-imidazol-4-yl)propanoic acid
Chemical Formula C9H14N4O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Polypeptides
Sub Class
  • Dipeptides
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); carboxylic acid; secondary carboxylic acid amide; aromatic compound; heterocyclic compound
Biofunction
  • Component of beta-Alanine metabolism; Component of Histidine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 226.232
Monoisotopic Molecular Weight 226.106583
Isomeric SMILES NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O
Canonical SMILES NCCC(=O)NC(CC1=CN=CN1)C(O)=O
KEGG Compound ID C00386 Link Image
BioCyc ID CARNOSINE Link Image
BiGG ID 1800369 Link Image
Wikipedia Link Carnosine Link Image
METLIN ID 38 Link Image
PubChem Compound 439224 Link Image
PubChem Substance 11366634 Link Image
ChEBI ID 15727 Link Image
CAS Registry Number 305-84-0
InChI Identifier InChI=1/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
Synthesis Reference Vezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6
Melting Point (Experimental) 253-256 oC
Experimental Water Solubility 384 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 11.1 mg/mL [Predicted by ALOGPS]; 82.1 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.96 [Predicted by ALOGPS]; -4.1 [Predicted by PubChem via XLOGP]; -1.81 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
Biofluid Location
  • Rumen
Tissue Location
Tissue References
Brain
Fibroblasts
Intestine
Kidney
Liver
Muscle
Neuron
Skeletal Muscle
Concentrations (Normal)
Biofluid Breast_Milk
Value 0.654325 +/- 0.01 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by DFI-MS in 2% milk
References
Biofluid Breast_Milk
Value 0.73 +/- 0.036 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by DFI-MS in 1% milk
References
Biofluid Breast_Milk
Value 0.697 +/- 0.01 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by DFI-MS in skim milk
References
Biofluid Breast_Milk
Value 0.52 +/- 0.011 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by DFI-MS in 3.25% milk
References
Biofluid Rumen
Value 0.47 +/- 0.24 uM
Age N/A
Sex N/A
Condition Normal
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names
  • Histidine Metabolism
HMDB Pathways
Name Histidine Metabolism
Image Show Link Image
KEGG Pathways
Name Histidine Metabolism
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SimCell Pathways
Name Histidine Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image