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Record Information
Version1.0
Creation Date2016-07-13 19:40:23 UTC
Update Date2016-07-20 20:48:22 UTC
LmdbLMDB00010
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarnosine
DescriptionCarnosine (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 ).
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 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
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9200000000-e1b627f2d6087f1a4f3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9110000000-a23fcd512ed705116d19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a6r-0590000000-3facdeb7a9f1b833cadfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-1900000000-a39c1a1f1db8549d69feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03e9-9500000000-0a9e5951251391cb0caaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03fr-0930000000-037f91ca363dacbc0112View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-d75632020730d38db12aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-eae5a77f232972048ea2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-08fr-0390000000-61159b9b20f5afda0d0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03fs-0930000000-2164b41d8882cd740337View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4j-0900000000-d36823b00135c9d452c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2d556024df911bfcf1f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0390000000-7a7d8e991b46e87abc36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0490200000-e7a68540cb7eb6b88020View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-0ea0b380dcef3109e0dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-d329921f45fac5494381View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-bf47d3f6eac10e087754View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0392411100-6efd739ab2e55ac98d81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-22bfeae9981523b0cbc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-35810c1e1756541bd16aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0190000000-a4df7b97ef1090978371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-8eb3d9ac409912a61228View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0w4i-0930000000-4568b16b1f6ed9a27f0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-1900000000-7771effc7ceb4499f395View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-6900000000-2a23069b75992b4bfcacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-01q9-9200000000-702c77c424d21cbeb2c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-0190000000-441d34f3fa359acb868eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Follicular Fluid
  • Meat
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
Follicular FluidDetected and Quantified68 +/- 4-100+/-2 uMNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified3.96+/-0.64 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified4.46+/-0.43 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified4.73+/-0.48 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified89.36+/-4.06 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified1802.96 +/- 87.68 uMNot AvailableBovine details
MeatDetected and Quantified2187.41 +/- 125.15 uMNot AvailableBovine details
MeatDetected and Quantified2492.74 +/- 320.38 uMNot AvailableBovine details
MeatDetected and Quantified3447.54 +/- 171.14 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected and Quantified15.03 uMNot AvailablePorcine details
PlasmaDetected and Quantified17.96 uMNot AvailablePorcine details
PlasmaDetected and Quantified21.64 uMNot AvailablePorcine details
PlasmaDetected and Quantified38.02 uMNot AvailablePorcine details
PlasmaDetected and Quantified29 +/- 3-31+/-7 uMNot AvailablePorcine details
PlasmaDetected and Quantified33 +/- 5-26+/-3 uMNot AvailablePorcine details
PlasmaDetected and Quantified38 +/- 6-46+/-8 uMNot AvailablePorcine details
Ruminal FluidDetected and Quantified0.47 +/- 0.24 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified2.0775 uMNot AvailablePorcine details
SerumDetected and Quantified1.503 uMNot AvailablePorcine details
SerumDetected and Quantified1.635 uMNot AvailablePorcine details
SerumDetected and Quantified2.696 uMNot AvailablePorcine details
SerumDetected and Quantified110 +/- 20 uMNot AvailablePorcine details
SerumDetected and Quantified19 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified24.9 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified27.4 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified31 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
DrugBank IDDB11695
HMDB IDHMDB0000033
FooDB IDFDB009278
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1800369
BioCyc IDCARNOSINE
METLIN ID38
PDB IDNot Available
Wikipedia LinkCarnosine
Chemspider ID388363
ChEBI ID15727
PubChem Compound ID439224
Kegg Compound IDC00386
YMDB IDYMDB01555
ECMDB IDECMDB00033
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hipkiss AR: Would carnosine or a carnivorous diet help suppress aging and associated pathologies? Ann N Y Acad Sci. 2006 May;1067:369-74. [16804013 ]
  2. 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. [16406688 ]