| 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 ). 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- b-Alanyl-L-histidine
- b-Alanylhistidine
- beta-Alanyl-L-histidine
- beta-Alanylhistidine
- Carnosine
- Ignotine
- Karnozin
- Karnozzn
- L-Carnosine
- N-(3-Aminopropanoyl)histidine
- N-(b-Alanyl)-L-histidine
- N-b-Alanyl-L-Histidine
- N-beta-Alanyl-L-Histidine
- 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
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| Direct Parent |
Hybrid Peptides |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Histidine metabolism
- Component of beta-Alanine metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| 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 |
|
| 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 |
|
| Biofluid Locations |
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Fibroblasts
- Intestine
- Neuron
- Kidney
- Liver
- Brain
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| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
6.54 +/- 1.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
3.1 +/- 7.5 uM |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.84 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.0 (0.0-2.2) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
5.5 (1.4-12.6) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
19.97 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.2 +/- 4.36 umol/mmol creatinine |
Children (1-13 year old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.5 +/- 2.7 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
4.0 +/- 2.5 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
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 |
|
0.014-0.032 umol/mmol creatinine |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.1+/-0.5 umol/mmol creatinine |
Not Specified |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
3.28 +/- 0.91 uM |
Elderly (>65 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
84.8 (56.5-113.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Carnosinuria |
Not Available |
| Urine |
Detected and Quantified |
|
18.8 +/- 10.31 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
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
- 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
|
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| Associated OMIM IDs |
|
| External Links |
| 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  |
| KEGG Compound ID |
C00386  |
| BioCyc ID |
CARNOSINE  |
| BiGG ID |
1800369  |
| Wikipedia Link |
Carnosine  |
| NuGOwiki Link |
HMDB00033  |
| Metagene Link |
HMDB00033  |
| METLIN ID |
38  |
| PubChem Compound |
439224  |
| PDB ID |
Not Available |
| ChEBI ID |
15727  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- Furst P: Amino acid metabolism in uremia. J Am Coll Nutr. 1989 Aug;8(4):310-23.
Pubmed: 2674258
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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