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| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:18:44 UTC |
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| Update Date | 2020-06-04 21:54:05 UTC |
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| BMDB ID | BMDB0000033 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Carnosine |
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| Description | Carnosine, also known as b-alanylhistidine or ignotine, 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. Carnosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Carnosine exists in all living species, ranging from bacteria to humans. Carnosine is a potentially toxic compound. Carnosine has been found to be associated with several diseases known as eosinophilic esophagitis, crohn's disease, ulcerative colitis, and alzheimer's disease; also carnosine has been linked to the inborn metabolic disorders including carnosinuria. |
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| Structure | |
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| Synonyms | | Value | Source |
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| Nalpha-(beta-alanyl)-L-histidine | ChEBI | | Nalpha-(b-alanyl)-L-histidine | Generator | | Nalpha-(β-alanyl)-L-histidine | Generator | | b-Alanyl-L-histidine | HMDB | | b-Alanylhistidine | HMDB | | beta-Alanyl-L-histidine | HMDB | | beta-Alanylhistidine | HMDB | | Ignotine | HMDB | | Karnozin | HMDB | | Karnozzn | HMDB | | L-Carnosine | HMDB | | N-(3-Aminopropanoyl)histidine | HMDB | | N-(b-Alanyl)-L-histidine | HMDB | | N-b-Alanyl-L-histidine | HMDB | | N-beta-Alanyl-L-histidine | HMDB | | Sevitin | HMDB | | Carnosine, (D-his)-isomer | HMDB | | Hydrochloride, carnosine | HMDB | | L Carnosine | HMDB | | Carnosine hydrochloride | HMDB | | beta Alanylhistidine | HMDB |
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| Chemical Formula | C9H14N4O3 |
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| Average Molecular Weight | 226.2325 |
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| Monoisotopic Molecular Weight | 226.106590334 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 305-84-0 |
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| SMILES | Not Available |
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| 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 |
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| InChI Key | CQOVPNPJLQNMDC-ZETCQYMHSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Peptidomimetics |
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| Sub Class | Hybrid peptides |
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| Direct Parent | Hybrid peptides |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| 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 |
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| Predicted Properties | Not Available |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Brain
- Colostrum
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Milk
- Muscle
- Neuron
- Placenta
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 30 +/- 12 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 15-20 uM | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 393 +/- 130 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 22085 +/- 4859 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.48 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.50 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.46 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.46 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1802.96 +/- 87.68 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 2187.41 +/- 125.15 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 89360 +/- 4060 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 4730 +/- 480 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 2492.74 +/- 320.38 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 3960 +/- 640 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 4460 +/- 430 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 3447.54 +/- 171.14 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1715-3619 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 9900 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 433-701 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 9690-13658 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.47 +/- 0.24 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.47 +/- 0.24 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 21958 +/- 3048 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 12 +/- 3 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
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| External Links |
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| HMDB ID | HMDB0000033 |
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| DrugBank ID | DB11695 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012937 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 388363 |
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| KEGG Compound ID | C00386 |
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| BioCyc ID | CARNOSINE |
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| BiGG ID | 1800369 |
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| Wikipedia Link | Carnosine |
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| METLIN ID | 38 |
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| PubChem Compound | 439224 |
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| PDB ID | Not Available |
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| ChEBI ID | 15727 |
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| References |
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| Synthesis Reference | Vezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6 |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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