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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:20 UTC
NP-MRD IDNP0000687
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarnosine
DescriptionCarnosine, 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. β-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: β-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
Thumb
Synonyms
ValueSource
(2S)-2-(3-Aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acidChEBI
beta-Alanyl-L-histidineChEBI
IgnotineChEBI
KarnozinChEBI
KarnozznChEBI
L-CarnosineChEBI
N-(3-Aminopropanoyl)-L-histidineChEBI
N-2-mChEBI
N-beta-Alanyl-L-histidineChEBI
Nalpha-(beta-alanyl)-L-histidineChEBI
(2S)-2-(3-Aminopropanamido)-3-(1H-imidazol-4-yl)propanoateGenerator
b-Alanyl-L-histidineGenerator
Β-alanyl-L-histidineGenerator
N-b-Alanyl-L-histidineGenerator
N-Β-alanyl-L-histidineGenerator
Nalpha-(b-alanyl)-L-histidineGenerator
Nalpha-(β-alanyl)-L-histidineGenerator
b-AlanylhistidineHMDB
beta-AlanylhistidineHMDB
N-(3-Aminopropanoyl)histidineHMDB
N-(b-Alanyl)-L-histidineHMDB
SevitinHMDB
Carnosine, (D-his)-isomerHMDB
Hydrochloride, carnosineHMDB
L CarnosineHMDB
Carnosine hydrochlorideHMDB
beta AlanylhistidineHMDB
Chemical FormulaC9H14N4O3
Average Mass226.2325 Da
Monoisotopic Mass226.10659 Da
IUPAC Name(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid
Traditional Nameβ-alanyl-L-histidine
CAS Registry Number305-84-0
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 KeyCQOVPNPJLQNMDC-ZETCQYMHSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-02View Spectrum
Species
Species of Origin
  • Animalia
  • Species Where Detected
    Species NameSourceReference
    Homo sapiens (Urine)KNApSAcK Database
    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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point253 - 256 °CNot Available
    Boiling Point656.00 to 657.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
    Water Solubility384 mg/mLNot Available
    LogP-2.972 (est)The Good Scents Company Information System
    Predicted Properties
    PropertyValueSource
    Water Solubility11.1 g/LALOGPS
    logP-3ALOGPS
    logP-4.5ChemAxon
    logS-1.3ALOGPS
    pKa (Strongest Acidic)3.37ChemAxon
    pKa (Strongest Basic)9.13ChemAxon
    Physiological Charge1ChemAxon
    Hydrogen Acceptor Count5ChemAxon
    Hydrogen Donor Count4ChemAxon
    Polar Surface Area121.1 ŲChemAxon
    Rotatable Bond Count6ChemAxon
    Refractivity55.56 m³·mol⁻¹ChemAxon
    Polarizability22.37 ųChemAxon
    Number of Rings1ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0000033
    DrugBank IDDB11695
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB012937
    KNApSAcK IDC00052222
    Chemspider ID388363
    KEGG Compound IDC00386
    BioCyc IDCARNOSINE
    BiGG ID1800369
    Wikipedia LinkCarnosine
    METLIN ID38
    PubChem Compound439224
    PDB IDNot Available
    ChEBI ID15727
    Good Scents IDrw1253461
    References
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    6. Furst P: Amino acid metabolism in uremia. J Am Coll Nutr. 1989 Aug;8(4):310-23. [PubMed:2674258 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    17. Hipkiss AR: Would carnosine or a carnivorous diet help suppress aging and associated pathologies? Ann N Y Acad Sci. 2006 May;1067:369-74. [PubMed:16804013 ]
    18. Guney Y, Turkcu UO, Hicsonmez A, Andrieu MN, Guney HZ, Bilgihan A, Kurtman C: Carnosine may reduce lung injury caused by radiation therapy. Med Hypotheses. 2006;66(5):957-9. Epub 2006 Jan 10. [PubMed:16406688 ]