NP-MRD: Showing NP-Card for Homocarnosine (NP0000182)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:13:29 UTC

NP-MRD ID

NP0000182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homocarnosine

Description

Homocarnosine is a normal human metabolite, the brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. (PMID 1266573 ). Increased concentration of CSF homocarnosine has been found in familial spastic paraplegia. (PMID 842287 ). Homocarnosinosis (an inherited disorder, OMIM 236130 ) is characterized by an elevated level of the dipeptide homocarnosine (Hca) in the Cerebrospinal fluid (CSF) and the brain and by carnosinuria and serum carnosinase deficiency, and can co-exist with paraplegia, retinitis pigmentosa, and a progressive mental deficiency. (PMID 3736769 ). In glial tumors of human brain the content of homocarnosine has been found to be lower than in brain tissue (PMID 1032224 ), while an increase in content of homocarnosine was observed in brain tissue of animals under experimental trauma of cranium. (PMID 1025883 ).

Structure

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

HMDB0000745
     RDKit          3D
Homocarnosine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.4432    1.1043    0.3788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    0.4174    1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.0076    1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -1.2739   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -0.6616   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9248   -0.0145    0.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -0.8055   -1.2477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982   -0.2256   -1.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7300   -0.8929   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262   -0.3774   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770    0.6773    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8907    0.8593    0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2540   -0.0719   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994   -0.8323   -0.8764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    1.2352   -1.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    1.7802   -0.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853    2.0382   -1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9519    1.2271   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.8368    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.0051    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672    0.4049    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -1.4225    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -1.5668    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -1.0363   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604   -2.3889   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.3686   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125   -0.4703   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -1.9694   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -0.8218    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    1.2847    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4877    1.6073    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2573   -0.1716   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    2.9014   -1.6611 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 17 33  1  0
M  END

L-Histidine, N-(4-amino-1-oxobutyl)- .mol
  Mrv1652305271900152D          

 17 17  0  0  0  0            999 V2000
    0.7761    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4906   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2050   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0982    0.5795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587   -0.7481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5107   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1

> <INCHI_KEY>
CCLQKVKJOGVQLU-QMMMGPOBSA-N

> <FORMULA>
C10H16N4O3

> <MOLECULAR_WEIGHT>
240.259

> <EXACT_MASS>
240.122240398

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.490377706444548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

> <ALOGPS_LOGP>
-2.85

> <JCHEM_LOGP>
-3.869733480628142

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.022486755740385

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4452730189233747

> <JCHEM_PKA_STRONGEST_BASIC>
9.99065125450378

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000001

> <JCHEM_REFRACTIVITY>
59.75120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000745
     RDKit          3D
Homocarnosine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.4432    1.1043    0.3788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    0.4174    1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.0076    1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -1.2739   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -0.6616   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9248   -0.0145    0.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -0.8055   -1.2477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982   -0.2256   -1.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7300   -0.8929   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262   -0.3774   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770    0.6773    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8907    0.8593    0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2540   -0.0719   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994   -0.8323   -0.8764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    1.2352   -1.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    1.7802   -0.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853    2.0382   -1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9519    1.2271   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.8368    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.0051    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672    0.4049    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -1.4225    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -1.5668    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -1.0363   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604   -2.3889   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.3686   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125   -0.4703   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -1.9694   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -0.8218    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    1.2847    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4877    1.6073    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2573   -0.1716   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    2.9014   -1.6611 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: L-Histidine, N-(4-amino-1-oxobutyl)- .mol         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.449   0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.115  -1.540   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.449  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.782  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.116  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.277   0.762   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.783   1.082   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.553  -0.252   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.523  -1.396   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.782   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.115   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.219  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.552  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.886  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.220  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.219   0.770   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -6.553  -0.770   0.000  0.00  0.00           N+0
CONECT    1    3   10   11                                                  
CONECT    2    3   12                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12   13   16    2                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   17                                                       
CONECT   16   12                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0000745
HETATM    1  N1  UNL     1       4.443   1.104   0.379  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.688   0.417   1.398  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.410  -1.008   1.081  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.634  -1.274  -0.155  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.293  -0.662  -0.144  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.925  -0.014   0.855  1.00  0.00           O  
HETATM    7  N2  UNL     1       0.438  -0.805  -1.248  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.898  -0.226  -1.302  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.730  -0.893  -0.230  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.126  -0.377  -0.187  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.577   0.677   0.578  1.00  0.00           C  
HETATM   12  N3  UNL     1      -4.891   0.859   0.358  1.00  0.00           N  
HETATM   13  C9  UNL     1      -5.254  -0.072  -0.533  1.00  0.00           C  
HETATM   14  N4  UNL     1      -4.199  -0.832  -0.876  1.00  0.00           N  
HETATM   15  C10 UNL     1      -0.758   1.235  -1.120  1.00  0.00           C  
HETATM   16  O2  UNL     1       0.355   1.780  -0.957  1.00  0.00           O  
HETATM   17  O3  UNL     1      -1.885   2.038  -1.129  1.00  0.00           O  
HETATM   18  H1  UNL     1       3.952   1.227  -0.511  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.429   0.837   0.334  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.812   1.005   1.733  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.367   0.405   2.304  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.821  -1.422   1.950  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.361  -1.567   1.093  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.176  -1.036  -1.092  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.460  -2.389  -0.207  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.799  -1.369  -2.076  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.313  -0.470  -2.316  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.796  -1.969  -0.501  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.254  -0.822   0.749  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.969   1.285   1.267  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.488   1.607   0.822  1.00  0.00           H  
HETATM   32  H15 UNL     1      -6.257  -0.172  -0.902  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.965   2.901  -1.661  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6    6    7
CONECT    7    8   26
CONECT    8    9   15   27
CONECT    9   10   28   29
CONECT   10   11   11   14
CONECT   11   12   30
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0000745
     RDKit          3D
Homocarnosine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.4432    1.1043    0.3788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    0.4174    1.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.0076    1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -1.2739   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -0.6616   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9248   -0.0145    0.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -0.8055   -1.2477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982   -0.2256   -1.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7300   -0.8929   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262   -0.3774   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770    0.6773    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8907    0.8593    0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2540   -0.0719   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994   -0.8323   -0.8764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    1.2352   -1.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    1.7802   -0.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853    2.0382   -1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9519    1.2271   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.8368    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.0051    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672    0.4049    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -1.4225    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -1.5668    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -1.0363   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604   -2.3889   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.3686   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125   -0.4703   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -1.9694   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -0.8218    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    1.2847    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4877    1.6073    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2573   -0.1716   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    2.9014   -1.6611 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 17 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-Homocarnosine	ChEBI
(S)-Homocarnosine	ChEBI
gamma-Aminobutyryl-L-his	ChEBI
N-(4-Aminobutanoyl)-(S)-histidine	ChEBI
N-(4-Aminobutyryl)-L-histidine	ChEBI
N(alpha)-(4-Aminobutyryl)-L-histidine	ChEBI
L-Homocarnosine	Kegg
gamma-Aminobutyryl histidine	Kegg
N-(4-Amino-1-oxobutyryl)histidine	Kegg
g-Aminobutyryl-L-his	Generator
Γ-aminobutyryl-L-his	Generator
N(a)-(4-Aminobutyryl)-L-histidine	Generator
N(Α)-(4-aminobutyryl)-L-histidine	Generator
g-Aminobutyryl histidine	Generator
Γ-aminobutyryl histidine	Generator
gamma-Aminobutyryl-L-histidine	HMDB
Homocarnosine sulfate	HMDB
g-Aminobutyryl-L-histidine	HMDB
g-Aminobutyrylhistidine	HMDB
gamma-Aminobutyrylhistidine	HMDB
N-(4-Aminobutyryl)-histidine	HMDB

Chemical Formula

C₁₀H₁₆N₄O₃

Average Mass

240.2590 Da

Monoisotopic Mass

240.12224 Da

IUPAC Name

(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

Traditional Name

(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid

CAS Registry Number

3650-73-5

SMILES

NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1

InChI Key

CCLQKVKJOGVQLU-QMMMGPOBSA-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
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

Not Available

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
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
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

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
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acyl-amine
Fatty amide
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Amino acid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Organooxygen compound
Primary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

L-histidine derivative (CHEBI:85981 )
N-acyl-L-alpha-amino acid (CHEBI:85981 )
homocarnosine (CHEBI:85981 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.37 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	9.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	59.75 m³·mol⁻¹	ChemAxon
Polarizability	24.49 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

HMDB0000745

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022217

KNApSAcK ID

Not Available

Chemspider ID

8418848

KEGG Compound ID

C00884

BioCyc ID

CPD-12185

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

270

PubChem Compound

10243361

PDB ID

Not Available

ChEBI ID

85981

Good Scents ID

Not Available

References

General References

Lenney JF, Peppers SC, Kucera CM, Sjaastad O: Homocarnosinosis: lack of serum carnosinase is the defect probably responsible for elevated brain and CSF homocarnosine. Clin Chim Acta. 1983 Aug 15;132(2):157-65. [PubMed:6616870 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Petroff OA, Mattson RH, Behar KL, Hyder F, Rothman DL: Vigabatrin increases human brain homocarnosine and improves seizure control. Ann Neurol. 1998 Dec;44(6):948-52. [PubMed:9851440 ]
Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]
Rothman DL, Behar KL, Prichard JW, Petroff OA: Homocarnosine and the measurement of neuronal pH in patients with epilepsy. Magn Reson Med. 1997 Dec;38(6):924-9. [PubMed:9402193 ]
Pearl PL, Novotny EJ, Acosta MT, Jakobs C, Gibson KM: Succinic semialdehyde dehydrogenase deficiency in children and adults. Ann Neurol. 2003;54 Suppl 6:S73-80. [PubMed:12891657 ]
Tell G, Bohlen P, Schechter PJ, Koch-Weser J, Agid Y, Bonnet AM, Coquillat G, Chazot G, Fischer C: Treatment of Huntington disease with gamma-acetylenic GABA an irreversible inhibitor of GABA-transaminase: increased CSF GABA and homocarnosine without clinical amelioration. Neurology. 1981 Feb;31(2):207-11. [PubMed:6258106 ]
Promyslov MSh, Mirzoian RA: [Homocarnosine metabolism in brain tissue]. Vopr Biokhim Mozga. 1976;11:71-7. [PubMed:1032224 ]
Iurovskii SL, Orlov VI, Pogorelova TN, Drukker NA, Madan M: [Homocarnosine of the amniotic fluid as an indicator of fetal cerebral lesions]. Akush Ginekol (Mosk). 1989 Sep;(9):45-7. [PubMed:2596637 ]
Menachem EB, Persson LI, Schechter PJ, Haegele KD, Huebert N, Hardenberg J, Dahlgren L, Mumford JP: Effects of single doses of vigabatrin on CSF concentrations of GABA, homocarnosine, homovanillic acid and 5-hydroxyindoleacetic acid in patients with complex partial epilepsy. Epilepsy Res. 1988 Mar-Apr;2(2):96-101. [PubMed:3143561 ]
Perry TL, Kish SJ, Sjaastad O, Gjessing LR, Nesbakken R, Schrader H, Loken AC: Homocarnosinosis: increased content of homocarnosine and deficiency of homocarnosinase in brain. J Neurochem. 1979 Jun;32(6):1637-40. [PubMed:448356 ]
Promyslov MSh, Mirzoian RA: [Study of homocarnosine metabolism in the brain tissue in diseases of the nervous system]. Vopr Med Khim. 1976 Mar-Apr;22(2):209-12. [PubMed:1025883 ]
Manyam BV, Bhatt MH, Moore WD, Devleschoward AB, Anderson DR, Calne DB: Bilateral striopallidodentate calcinosis: cerebrospinal fluid, imaging, and electrophysiological studies. Ann Neurol. 1992 Apr;31(4):379-84. [PubMed:1586138 ]
Sjaastad O, Gjessing L, Berstad JR, Gjesdahl P: Homocarnosinosis. 3. Spinal fluid amino acids in familial spastic paraplegia. Acta Neurol Scand. 1977 Feb;55(2):158-62. [PubMed:842287 ]
Sjaastad O, Berstad J, Gjesdahl P, Gjessing L: Homocarnosinosis. 2. A familial metabolic disorder associated with spastic paraplegia, progressive mental deficiency, and retinal pigmentation. Acta Neurol Scand. 1976 Apr;53(4):275-90. [PubMed:1266573 ]
Lunde HA, Gjessing LR, Sjaastad O: Homocarnosinosis: influence of dietary restriction of histidine. Neurochem Res. 1986 Jun;11(6):825-38. [PubMed:3736769 ]

Showing NP-Card for Homocarnosine (NP0000182)

MOL for NP0000182 (Homocarnosine)

3D MOL for NP0000182 (Homocarnosine)

3D SDF for NP0000182 (Homocarnosine)

3D-SDF for NP0000182 (Homocarnosine)

PDB for NP0000182 (Homocarnosine)

3D PDB for NP0000182 (Homocarnosine)

SMILES for NP0000182 (Homocarnosine)

INCHI for NP0000182 (Homocarnosine)

Structure for NP0000182 (Homocarnosine)

3D Structure for NP0000182 (Homocarnosine)