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Carnosine information


Carnosine
Names
IUPAC name
β-Alanylhistidine
Systematic IUPAC name
(2S)-2-(3-Aminopropanamido)-3-(3H-imidazol-4-yl)propanoic acid
Other names
β-Alanyl-L-histidine
Identifiers
CAS Number
  • 305-84-0 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:15727 checkY
ChEMBL
  • ChEMBL242948 checkY
ChemSpider
  • 388363 checkY
ECHA InfoCard 100.005.610 Edit this at Wikidata
IUPHAR/BPS
  • 4559
KEGG
  • C00386 checkY
PubChem CID
  • 439224
UNII
  • 8HO6PVN24W checkY
CompTox Dashboard (EPA)
  • DTXSID80879594 Edit this at Wikidata
InChI
  • 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 checkY
    Key: CQOVPNPJLQNMDC-ZETCQYMHSA-N checkY
  • 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
    Key: CQOVPNPJLQNMDC-ZETCQYMHBX
SMILES
  • O=C(O)C(NC(=O)CCN)Cc1c[nH]cn1
  • c1c(nc[nH]1)C[C@@H](C(=O)O)NC(=O)CCN
Properties
Chemical formula
C9H14N4O3
Molar mass 226.236 g·mol−1
Appearance Crystalline solid
Melting point 253 °C (487 °F; 526 K) (decomposition)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Carnosine (beta-alanyl-L-histidine) is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues.[citation needed] Carnosine was discovered by Russian chemist Vladimir Gulevich.[1]

Carnosine is naturally produced by the body in the liver[2] from beta-alanine and histidine. Like carnitine, carnosine is composed of the root word carn, meaning "flesh", alluding to its prevalence in meat.[3] There are no plant-based sources of carnosine.[4] Carnosine is readily available as a synthetic nutritional supplement.

  1. ^ Gulewitsch, Wl.; Amiradžibi, S. (1900). "Ueber das Carnosin, eine neue organische Base des Fleischextractes". Berichte der Deutschen Chemischen Gesellschaft. 33 (2): 1902–1903. doi:10.1002/cber.19000330275.
  2. ^ Trexler, Eric T.; Smith-Ryan, Abbie E.; Stout, Jeffrey R.; Hoffman, Jay R.; Wilborn, Colin D.; Sale, Craig; Kreider, Richard B.; Jäger, Ralf; Earnest, Conrad P.; Bannock, Laurent; Campbell, Bill (2015-07-15). "International society of sports nutrition position stand: Beta-Alanine". Journal of the International Society of Sports Nutrition. 12: 30. doi:10.1186/s12970-015-0090-y. ISSN 1550-2783. PMC 4501114. PMID 26175657.
  3. ^ Hipkiss, A. R. (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Annals of the New York Academy of Sciences. 1067 (1): 361–8. Bibcode:2006NYASA1067..361H. doi:10.1196/annals.1354.051. PMID 16804012. S2CID 41175541.
  4. ^ Alan R. Hipkiss (2009). "Chapter 3: Carnosine and Its Possible Roles in Nutrition and Health". Advances in Food and Nutrition Research.

and 22 Related for: Carnosine information

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Carnosine

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Carnosine (beta-alanyl-L-histidine) is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle...

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Acetylcarnosine

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compound chemically related to the dipeptide carnosine. The NAC molecular structure is identical to carnosine with the exception that it carries an additional...

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Carnosine synthase

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Carnosine synthase (EC 6.3.2.11) is an enzyme that catalyzes the chemical reaction ATP + L-histidine + beta-alanine ⇌ {\displaystyle \rightleftharpoons...

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Anserine

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3-methylhistidine. Anserine is a derivative of carnosine, which has been methylated. Both anserine and carnosine chelate copper. Due to its methylation, anserine...

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Histidine

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certain methyltransferase enzymes. Histidine is also a precursor for carnosine biosynthesis, which is a dipeptide found in skeletal muscle. In Actinomycetota...

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Carnosinemia

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enzyme that splits dipeptides into their two amino acid constituents). Carnosine is a dipeptide composed of beta-alanine and histidine, and is found in...

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Geroprotector

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life span of animals. Some possible geroprotectors include melatonin, carnosine, metformin, rapamycin, nicotinamide mononucleotide (NMN) and delta sleep-inducing...

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Cataract

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"The effect of a topical antioxidant formulation including N-acetyl carnosine on canine cataract: a preliminary study". Veterinary Ophthalmology. 9...

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Vladimir Gulevich

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September 1933) was a Russian Empire and Soviet biochemist who first isolated carnosine from mammalian muscle. Gulevich graduated in 1890 and received the degree...

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GADL1

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β-alanine, GADL1 consequently plays a role in the production of carnosine. Carnosine and taurine have multiple biological functions such as calcium regulation...

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Gulf War syndrome

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investigating yoga as a treatment for GWI. An amino acid supplement containing L-carnosine was found to reduce irritable bowel syndrome-associated diarrhea in a...

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Methylsulfonylmethane

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the effects of a nutraceutical composed of MSM, hyaluronic acid, and L-carnosine. The results from RCT showed broad improvements in facial skin hydration...

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Cytoprotection

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analogue), bismuth chelate (tri-potassium di-citrato bismuthate) and zinc L-carnosine. "MeSH Heading: Cytoprotection". Medical Subject Headings. United States...

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Amino acid

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with the structure NH+3−CXY−CXY−CO−2, such as β-alanine, a component of carnosine and a few other peptides, are β-amino acids. Ones with the structure...

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CNDP1

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6521–31. doi:10.1074/jbc.M209764200. PMID 12473676. "Entrez Gene: CNDP1 carnosine dipeptidase 1 (metallopeptidase M20 family)". Lenney JF, Peppers SC, Kucera...

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Dipeptide

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(N-L-α-aspartyl-L-phenylalanine 1-methyl ester) is an artificial sweetener. Carnosine (beta-alanyl-L-histidine) and Anserine (beta-alanyl-N-methyl histidine)...

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NAC

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Corporation, Salt Lake City, Utah, U.S N-Acetylcarnosine, a compound related to carnosine N-Acetylcysteine, a medication Nucleus accumbens, a region in the brain...

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Cytosol nonspecific dipeptidase

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Cytosolic non-specific dipeptidase (EC 3.4.13.18) also known as carnosine dipeptidase 2 is an enzyme that in humans is encoded by the CNDP2 gene. This...

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Conditions comorbid to autism spectrum disorders

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Several other treatments that have antioxidant properties, including carnosine, have also been reported to significantly improve ASD behaviors, suggesting...

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Autism therapies

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supplements were hypothesized 'to relieve autism symptoms', including BDTH2, carnosine, cholesterol, cyproheptadine, D-cycloserine, folic acid, glutathione,...

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C9H14N4O3

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C9H14N4O3 (molar mass: 226.24 g/mol, exact mass: 226.1066 u) may refer to: Carnosine Nimorazole This set index page lists chemical structure articles associated...

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Colostrum

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Daniel S.; Thatcher, Rhys; Playford, Raymond J. (August 2016). "Zinc carnosine works with bovine colostrum in truncating heavy exercise–induced increase...

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