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Human Metabolome Database Version 3.5

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Showing metabocard for Carnosine (HMDB00033)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-13 17:07:15 -0600
HMDB ID HMDB00033
Secondary Accession Numbers None
Metabolite Identification
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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. b-Alanyl-L-histidine
  2. b-Alanylhistidine
  3. beta-Alanyl-L-histidine
  4. beta-Alanylhistidine
  5. Carnosine
  6. Ignotine
  7. Karnozin
  8. Karnozzn
  9. L-Carnosine
  10. N-(3-Aminopropanoyl)histidine
  11. N-(b-Alanyl)-L-histidine
  12. N-b-Alanyl-L-Histidine
  13. N-beta-Alanyl-L-Histidine
  14. Sevitin
Chemical Formula C9H14N4O3
Average Molecular Weight 226.2325
Monoisotopic Molecular Weight 226.106590334
IUPAC Name (2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid
Traditional IUPAC Name (2S)-2-(3-aminopropanamido)-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry Number 305-84-0
SMILES NCCC(=O)N[C@@H](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)/t7-/m0/s1
InChI Key CQOVPNPJLQNMDC-ZETCQYMHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptidomimetics
Sub Class Hybrid Peptides
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Beta Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
Direct Parent Hybrid Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Histidine metabolism
  • Component of beta-Alanine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 253 - 256 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 384 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11.1 g/L ALOGPS
LogP -2.96 ALOGPS
LogP -4.5 ChemAxon
LogS -1.31 ALOGPS
pKa (strongest acidic) 3.37 ChemAxon
pKa (strongest basic) 9.13 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 121.1 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 55.56 ChemAxon
Polarizability 22.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Kidney
  • Liver
  • Brain
Pathways
Name SMPDB Link KEGG Link
Beta-Alanine Metabolism SMP00007 map00410 Link_out
Histidine Metabolism SMP00044 map00340 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
6.54 +/- 1.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
3.1 +/- 7.5 uM Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
1.84 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.0 (0.0-2.2) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
5.5 (1.4-12.6) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
19.97 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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3.2 +/- 4.36 umol/mmol creatinine Children (1-13 year old) Female Normal Not Available
Urine Detected and Quantified
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3.5 +/- 2.7 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
4.0 +/- 2.5 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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1.2 (0.2-4.1) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Urine Detected and Quantified
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0.014-0.032 umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
Article_icon
1.1+/-0.5 umol/mmol creatinine Not Specified Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
3.28 +/- 0.91 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
Article_icon
84.8 (56.5-113.0) umol/mmol creatinine Adult (>18 years old) Both Carnosinuria Not Available
Urine Detected and Quantified
Article_icon
18.8 +/- 10.31 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
Article_icon
56.56-113.1 umol/mmol creatinine Adult (>18 years old) Not Specified Carnosinuria Not Available
Associated Disorders and Diseases
Disease References
Carnosinuria
  • Furst P: Amino acid metabolism in uremia. J Am Coll Nutr. 1989 Aug;8(4):310-23. Pubmed: 2674258 Link_out
  • http://www.metagene.de/program/d.prg?mp=CARNOSINURIA
Alzheimer's disease
  • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB000511
    KNApSAcK ID Not Available
    Chemspider ID 388363 Link_out
    KEGG Compound ID C00386 Link_out
    BioCyc ID CARNOSINE Link_out
    BiGG ID 1800369 Link_out
    Wikipedia Link Carnosine Link_out
    NuGOwiki Link HMDB00033 Link_out
    Metagene Link HMDB00033 Link_out
    METLIN ID 38 Link_out
    PubChem Compound 439224 Link_out
    PDB ID Not Available
    ChEBI ID 15727 Link_out
    References
    Synthesis Reference Vezenkov, 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) Download (PDF)
    General References
    1. Park YJ, Volpe SL, Decker EA: Quantitation of carnosine in humans plasma after dietary consumption of beef. J Agric Food Chem. 2005 Jun 15;53(12):4736-9. Pubmed: 15941308 Link_out
    2. Guiotto A, Calderan A, Ruzza P, Borin G: Carnosine and carnosine-related antioxidants: a review. Curr Med Chem. 2005;12(20):2293-315. Pubmed: 16181134 Link_out
    3. Hipkiss AR, Preston JE, Himsworth DT, Worthington VC, Keown M, Michaelis J, Lawrence J, Mateen A, Allende L, Eagles PA, Abbott NJ: Pluripotent protective effects of carnosine, a naturally occurring dipeptide. Ann N Y Acad Sci. 1998 Nov 20;854:37-53. Pubmed: 9928418 Link_out
    4. Guiotto A, Calderan A, Ruzza P, Osler A, Rubini C, Jo DG, Mattson MP, Borin G: Synthesis and evaluation of neuroprotective alpha,beta-unsaturated aldehyde scavenger histidyl-containing analogues of carnosine. J Med Chem. 2005 Sep 22;48(19):6156-61. Pubmed: 16162015 Link_out
    5. Hipkiss AR, Brownson C: Carnosine reacts with protein carbonyl groups: another possible role for the anti-ageing peptide? Biogerontology. 2000;1(3):217-23. Pubmed: 11707898 Link_out
    6. Furst P: Amino acid metabolism in uremia. J Am Coll Nutr. 1989 Aug;8(4):310-23. Pubmed: 2674258 Link_out
    7. Lee YT, Hsu CC, Lin MH, Liu KS, Yin MC: Histidine and carnosine delay diabetic deterioration in mice and protect human low density lipoprotein against oxidation and glycation. Eur J Pharmacol. 2005 Apr 18;513(1-2):145-50. Epub 2005 Apr 2. Pubmed: 15878720 Link_out
    8. Hipkiss AR, Brownson C, Bertani MF, Ruiz E, Ferro A: Reaction of carnosine with aged proteins: another protective process? Ann N Y Acad Sci. 2002 Apr;959:285-94. Pubmed: 11976203 Link_out
    9. Mannion AF, Jakeman PM, Dunnett M, Harris RC, Willan PL: Carnosine and anserine concentrations in the quadriceps femoris muscle of healthy humans. Eur J Appl Physiol Occup Physiol. 1992;64(1):47-50. Pubmed: 1735411 Link_out
    10. Hipkiss AR, Brownson C, Carrier MJ: Carnosine, the anti-ageing, anti-oxidant dipeptide, may react with protein carbonyl groups. Mech Ageing Dev. 2001 Sep 15;122(13):1431-45. Pubmed: 11470131 Link_out
    11. Suzuki Y, Ito O, Mukai N, Takahashi H, Takamatsu K: High level of skeletal muscle carnosine contributes to the latter half of exercise performance during 30-s maximal cycle ergometer sprinting. Jpn J Physiol. 2002 Apr;52(2):199-205. Pubmed: 12139778 Link_out
    12. Kang JH, Kim KS, Choi SY, Kwon HY, Won MH, Kang TC: Protection by carnosine-related dipeptides against hydrogen peroxide-mediated ceruloplasmin modification. Mol Cells. 2002 Feb 28;13(1):107-12. Pubmed: 11911459 Link_out
    13. Willi SM, Zhang Y, Hill JB, Phelan MC, Michaelis RC, Holden KR: A deletion in the long arm of chromosome 18 in a child with serum carnosinase deficiency. Pediatr Res. 1997 Feb;41(2):210-3. Pubmed: 9029640 Link_out
    14. Tallon MJ, Harris RC, Boobis LH, Fallowfield JL, Wise JA: The carnosine content of vastus lateralis is elevated in resistance-trained bodybuilders. J Strength Cond Res. 2005 Nov;19(4):725-9. Pubmed: 16287364 Link_out
    15. Mozdzan M, Szemraj J, Rysz J, Nowak D: Antioxidant properties of carnosine re-evaluated with oxidizing systems involving iron and copper ions. Basic Clin Pharmacol Toxicol. 2005 May;96(5):352-60. Pubmed: 15853927 Link_out
    16. Jackson MC, Lenney JF: The distribution of carnosine and related dipeptides in rat and human tissues. Inflamm Res. 1996 Mar;45(3):132-5. Pubmed: 8689392 Link_out
    Enzymes
    Name: Myeloperoxidase
    Reactions:
    • donor + H2O2 = oxidized donor + 2 H2O [RN:R03532]
    Gene Name: MPO
    Uniprot ID: P05164 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-Ala-His dipeptidase
    Reactions:
    • Preferential hydrolysis of the beta-Ala!His dipeptide (carnosine), and also anserine, Xaa!His dipeptides and other dipeptides including homocarnosine [RN:R01166 R03288] ALL_REAC R01166 R03288 COFACTOR Citrate [CPD:C00158]
    • Cadmium [CPD:C01413]
    Gene Name: CNDP1
    Uniprot ID: Q96KN2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Histidine decarboxylase
    Reactions:
    • L-histidine = histamine + CO2 [RN:R01167]
    Gene Name: HDC
    Uniprot ID: P19113 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Vimentin
    Reactions:
      Gene Name: VIM
      Uniprot ID: P08670 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Heat shock 70 kDa protein 1A/1B
      Reactions:
        Gene Name: HSPA1A
        Uniprot ID: P08107 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Transporters
        Name: Solute carrier family 15 member 2
        Reactions:
        • --- []
        Gene Name: SLC15A2
        Uniprot ID: Q16348 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA