MiMeDB: Showing metabocard for Homocarnosine (MMDBc0029508)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:10 UTC

Update Date

2024-04-30 19:36:33 UTC

Metabolite ID

MMDBc0029508

Metabolite Identification

Common Name

Homocarnosine

Description

Homocarnosine is an intermediate of arginine and proline metabolism. tis converted from 4-amino-butanoate via aminoacylhistidine dipeptidase. It consists of gamma-aminobutyric acid and histidine.

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>
MMDBc0029508

> <DATABASE_NAME>
MIME

> <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

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	MeSH
Homocarnosine sulfate	MeSH
g-Aminobutyryl-L-histidine	HMDB
g-Aminobutyrylhistidine	HMDB
gamma-Aminobutyrylhistidine	HMDB
N-(4-Aminobutyryl)-histidine	HMDB

Molecular Formula

C₁₀H₁₆N₄O₃

Average Mass

240.259

Monoisotopic Mass

240.122240398

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-1920000000-a03e2c4f8b2c9d6a1635	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0920000000-e48ce78a12a5f4834686	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fk9-9710000000-32bfa6992d5a80f09a36	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1920000000-a03e2c4f8b2c9d6a1635	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0920000000-e48ce78a12a5f4834686	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-9710000000-32bfa6992d5a80f09a36	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9410000000-343b9389cd3a9e7656c5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000t-9620000000-f0df8a34f8155fd39194	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0910000000-b804d40537827898f4af	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-5900000000-26897d5ae957a9cb6b35	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03e9-9300000000-291e9d04c321015b9241	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0090000000-352076fb2d925fdf8d3d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0f79-0960000000-6efcaf43e71ab44953fa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-0900000000-4122cf33c566cb50775c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-03di-4900000000-499817ec7737f4f71264	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001i-9300000000-5e2839e6bf4597a45ad3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4l-0980000000-a0e96805123eef741d16	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4i-0900000000-bd852312bcfa93da513d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03di-2900000000-b0c96a1971d8e230da77	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-6900000000-086dfb0ef83a3e18d4c9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03yi-9300000000-cb8906cb50227e7ec5b5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0900000000-e3a22c7580a368d6849b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-eab8c998b760a5bc2d46	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000x-9000000000-d32f932f9d139b180e07	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0iki-0930000000-80b81755ee1a773ed3bb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0090000000-5b43effb3dfed505b61b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0f79-0960000000-52b5a3c482216dc5067d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-1490000000-abafa225b4c4cc6f1314	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-5930000000-d1e289dfa041a96af6e4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9400000000-3dc5fad146dc39014458	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0490000000-dfebe908fd4392611bb6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uej-3940000000-c7f4d398999fc797b544	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f7o-9500000000-f8ed9a520a7d500d0c1e	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Feces
Prostate
Urine

Tissue Locations

Brain
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192131	Beta-Ala-His dipeptidase	Unknown	Q96KN2	Homo sapiens
MMDBp0195610	Carnosine synthase 1	Unknown	A5YM72	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002568	gamma-Aminobutyric acid	Homocarnosine	carnosine synthase 1	VMH	448355 487087
MMDBr0002569	Homocarnosine	gamma-Aminobutyric acid	Not Available	VMH	2334521 4026801
MMDBr0005735	gamma-Aminobutyric acid	Homocarnosine	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Urine	Detected and Quantified	0.26		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.70	2.50	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0000745

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1111/j.1471-4159.1979.tb02273.x. [PubMed:448356 ]
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. doi: 10.1111/j.1600-0404.1977.tb05636.x. [PubMed:842287 ]
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 ]
Promyslov MSh, Mirzoian RA: [Homocarnosine metabolism in brain tissue]. Vopr Biokhim Mozga. 1976;11:71-7. [PubMed:1032224 ]
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. doi: 10.1111/j.1600-0404.1976.tb04348.x. [PubMed:1266573 ]
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. doi: 10.1002/ana.410310406. [PubMed:1586138 ]
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. doi: 10.1016/0920-1211(88)90025-3. [PubMed:3143561 ]
Lunde HA, Gjessing LR, Sjaastad O: Homocarnosinosis: influence of dietary restriction of histidine. Neurochem Res. 1986 Jun;11(6):825-38. doi: 10.1007/BF00965207. [PubMed:3736769 ]
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. doi: 10.1212/wnl.31.2.207. [PubMed:6258106 ]
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Showing metabocard for Homocarnosine (MMDBc0029508)

MOL for #<Metabolite:0x00007fecdd08c6a0>

3D MOL for #<Metabolite:0x00007fecdd08c6a0>

3D SDF for #<Metabolite:0x00007fecdd08c6a0>

3D-SDF for #<Metabolite:0x00007fecdd08c6a0>

PDB for #<Metabolite:0x00007fecdd08c6a0>

3D PDB for #<Metabolite:0x00007fecdd08c6a0>

SMILES for #<Metabolite:0x00007fecdd08c6a0>

INCHI for #<Metabolite:0x00007fecdd08c6a0>

Structure for #<Metabolite:0x00007fecdd08c6a0>

3D Structure for #<Metabolite:0x00007fecdd08c6a0>