NP-MRD: Showing NP-Card for Carnosine (NP0000687)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:20 UTC

NP-MRD ID

NP0000687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carnosine

Description

Carnosine, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    5.2833    0.0955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895   -0.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957   -0.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728   -1.6743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571   -0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931    1.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645    2.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555    3.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493    3.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    1.9453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149   -1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225   -0.8353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440   -3.3081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9124    1.4572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1481   -1.1302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    1.4533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255   -1.5344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1597    1.3172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317   -1.6704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -2.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -3.3042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -0.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6206   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982    1.8331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5374    4.5366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    1.3543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378   -3.4441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  2 20  1  0
  3 21  1  6
  3 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  6
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HMDB0000033
     RDKit          3D
Carnosine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2757    0.3752    1.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718    0.1898   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.7490   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282    0.0252   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.8908    0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    0.3622   -0.9404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.3149   -0.4527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205    0.7649    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.2833    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.1703    1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547   -0.5058    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7959   -0.2781    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    0.2057    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.9250   -1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344   -0.8096   -2.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.6561   -1.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981   -0.5653    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    0.8875    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -0.8818   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2675    0.7070   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.8302   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    0.4947   -2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    1.1188   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -1.1041    0.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197    1.2586    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    1.4995   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.2312    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -0.4614    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    0.4522   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -2.4092   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END


     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    5.2833    0.0955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895   -0.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957   -0.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728   -1.6743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571   -0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931    1.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645    2.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555    3.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493    3.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    1.9453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149   -1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225   -0.8353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440   -3.3081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9124    1.4572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1481   -1.1302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    1.4533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255   -1.5344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1597    1.3172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317   -1.6704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -2.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -3.3042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -0.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6206   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982    1.8331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5374    4.5366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    1.3543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378   -3.4441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  2 20  1  0
  3 21  1  6
  3 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  6
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END
> <DATABASE_ID>
NP0000687

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C9H14N4O3

> <MOLECULAR_WEIGHT>
226.2325

> <EXACT_MASS>
226.106590334

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.36612322974625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-2.96

> <JCHEM_LOGP>
-4.480241342175954

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.867210570530204

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.371243802200665

> <JCHEM_PKA_STRONGEST_BASIC>
9.12598191586239

> <JCHEM_POLAR_SURFACE_AREA>
121.1

> <JCHEM_REFRACTIVITY>
55.56190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-alanyl-L-histidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000033
     RDKit          3D
Carnosine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2757    0.3752    1.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718    0.1898   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.7490   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282    0.0252   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.8908    0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    0.3622   -0.9404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.3149   -0.4527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205    0.7649    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.2833    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.1703    1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547   -0.5058    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7959   -0.2781    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    0.2057    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.9250   -1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344   -0.8096   -2.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.6561   -1.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981   -0.5653    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    0.8875    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -0.8818   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2675    0.7070   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.8302   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    0.4947   -2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    1.1188   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -1.1041    0.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197    1.2586    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    1.4995   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.2312    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -0.4614    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    0.4522   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -2.4092   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8666.5538667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.2208668.207   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8666.5538665.899   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8667.8878665.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.2198665.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.5558665.126   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8671.8878665.899   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8667.8878663.586   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8667.8878668.207   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8669.2198667.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8667.8878669.747   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    8662.6338668.361   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8661.3878667.455   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8661.8638665.991   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8663.4038665.991   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.8798667.455   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1   16                                                       
CONECT    3    1    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14                                                       
CONECT   16   15   12    2                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0000033
HETATM    1  N1  UNL     1       4.276   0.375   1.019  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.372   0.190  -0.417  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.099   0.749  -1.044  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.928   0.025  -0.511  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.082  -0.891   0.326  1.00  0.00           O  
HETATM    6  N2  UNL     1       0.643   0.362  -0.940  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.566  -0.315  -0.453  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.420   0.765   0.163  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.693   0.283   0.716  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.967  -0.170   1.992  1.00  0.00           C  
HETATM   11  N3  UNL     1      -4.255  -0.506   2.056  1.00  0.00           N  
HETATM   12  C8  UNL     1      -4.796  -0.278   0.864  1.00  0.00           C  
HETATM   13  N4  UNL     1      -3.847   0.206   0.035  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.220  -0.925  -1.632  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.734  -0.810  -2.784  1.00  0.00           O  
HETATM   16  O3  UNL     1      -2.403  -1.656  -1.534  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.298  -0.565   1.492  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.134   0.887   1.373  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.495  -0.882  -0.670  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.268   0.707  -0.799  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.040   1.830  -0.930  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.144   0.495  -2.144  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.499   1.119  -1.633  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.303  -1.104   0.281  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.820   1.259   0.960  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.637   1.499  -0.637  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.244  -0.231   2.781  1.00  0.00           H  
HETATM   28  H12 UNL     1      -5.851  -0.461   0.613  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.064   0.452  -0.953  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.456  -2.409  -0.865  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5    5    6
CONECT    6    7   23
CONECT    7    8   14   24
CONECT    8    9   25   26
CONECT    9   10   10   13
CONECT   10   11   27
CONECT   11   12   12
CONECT   12   13   28
CONECT   13   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0000033
     RDKit          3D
Carnosine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2757    0.3752    1.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718    0.1898   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.7490   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282    0.0252   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.8908    0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    0.3622   -0.9404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.3149   -0.4527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4205    0.7649    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.2833    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.1703    1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547   -0.5058    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7959   -0.2781    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    0.2057    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.9250   -1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344   -0.8096   -2.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.6561   -1.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981   -0.5653    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    0.8875    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -0.8818   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2675    0.7070   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.8302   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    0.4947   -2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    1.1188   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -1.1041    0.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197    1.2586    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    1.4995   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -0.2312    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -0.4614    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    0.4522   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -2.4092   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 14 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-2-(3-Aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid	ChEBI
beta-Alanyl-L-histidine	ChEBI
Ignotine	ChEBI
Karnozin	ChEBI
Karnozzn	ChEBI
L-Carnosine	ChEBI
N-(3-Aminopropanoyl)-L-histidine	ChEBI
N-2-m	ChEBI
N-beta-Alanyl-L-histidine	ChEBI
Nalpha-(beta-alanyl)-L-histidine	ChEBI
(2S)-2-(3-Aminopropanamido)-3-(1H-imidazol-4-yl)propanoate	Generator
b-Alanyl-L-histidine	Generator
Β-alanyl-L-histidine	Generator
N-b-Alanyl-L-histidine	Generator
N-Β-alanyl-L-histidine	Generator
Nalpha-(b-alanyl)-L-histidine	Generator
Nalpha-(β-alanyl)-L-histidine	Generator
b-Alanylhistidine	HMDB
beta-Alanylhistidine	HMDB
N-(3-Aminopropanoyl)histidine	HMDB
N-(b-Alanyl)-L-histidine	HMDB
Sevitin	HMDB
Carnosine, (D-his)-isomer	HMDB
Hydrochloride, carnosine	HMDB
L Carnosine	HMDB
Carnosine hydrochloride	HMDB
beta Alanylhistidine	HMDB

Chemical Formula

C₉H₁₄N₄O₃

Average Mass

226.2325 Da

Monoisotopic Mass

226.10659 Da

IUPAC Name

(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

β-alanyl-L-histidine

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-02	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia magna	LOTUS Database	35616633
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Juncus roemerianus	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Opuntia ficus-indica	LOTUS Database	35616633
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:15727 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	253 - 256 °C	Not Available
Boiling Point	656.00 to 657.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	384 mg/mL	Not Available
LogP	-2.972 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	11.1 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	55.56 m³·mol⁻¹	ChemAxon
Polarizability	22.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000033

DrugBank ID

DB11695

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

439224

PDB ID

Not Available

ChEBI ID

15727

Good Scents ID

rw1253461

References

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 ]
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 ]
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 ]

Showing NP-Card for Carnosine (NP0000687)

MOL for NP0000687 (Carnosine)

3D MOL for NP0000687 (Carnosine)

3D SDF for NP0000687 (Carnosine)

3D-SDF for NP0000687 (Carnosine)

PDB for NP0000687 (Carnosine)

3D PDB for NP0000687 (Carnosine)

SMILES for NP0000687 (Carnosine)

INCHI for NP0000687 (Carnosine)

Structure for NP0000687 (Carnosine)

3D Structure for NP0000687 (Carnosine)