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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-06-05 20:16:03 UTC

Update Date

2022-09-22 18:34:33 UTC

HMDB ID

HMDB0240664

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoylcarnitine

Description

Benzoylcarnitine belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoylcarnitine is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acylcarnitines are useful in the diagnosis of genetic disorders such as fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency disorders (PMID: 12385891 ). Benzoylcarnitine is a metabolite of benzoate and has been identified in the urine of hyperammonemia patients treated with sodium benzoate and L-carnitine (PMID: 2609332 ).

Structure

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

HMDB0240664
     RDKit          3D
Benzoylcarnitine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.4626   -1.4263    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514   -0.0696    1.1665 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4017    0.2467    2.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -0.0721    2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.8728    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    0.5506   -0.9223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1467    1.6659   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    1.5121   -3.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    0.5695   -3.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    2.4769   -4.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394    0.3938   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.7804   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.7373   -1.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.8503   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -1.9995   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.0017    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -0.8992    0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    0.2458    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623    0.2361    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.0266    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3029   -1.9356    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -1.3774   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7648   -0.6674    2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.0178    2.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.6064    1.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108    0.0303    3.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.7977    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967   -1.0266    1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636    0.9572   -0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    1.9024    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.3909   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    1.7122   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    2.6578   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903    3.2808   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -2.8547   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -2.9038    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994   -0.9447    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.0950    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.1364    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 10 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  CHG  1   2   1
M  END


  Mrv1652306052021202D          

 19 19  0  0  0  0            999 V2000
   -4.6280   -0.1992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9140   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -0.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    0.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    0.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3420    1.0355    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -6.0601    0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3420    1.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950    1.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337   -1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6197   -1.8604    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.0477   -1.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860   -1.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -0.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  6  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 15  2  0  0  0  0
 19  4  1  0  0  0  0
M  CHG  2   7   1  13  -1
M  END
> <DATABASE_ID>
HMDB0240664

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO4/c1-15(2,3)10-12(9-13(16)17)19-14(18)11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3/t12-/m1/s1

> <INCHI_KEY>
AWUHAZDZHNWQAG-GFCCVEGCSA-N

> <FORMULA>
C14H19NO4

> <MOLECULAR_WEIGHT>
265.309

> <EXACT_MASS>
265.131408096

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.77387630071727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(benzoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.74

> <JCHEM_LOGP>
-2.3922061994717465

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9236797064362023

> <JCHEM_PKA_STRONGEST_BASIC>
-6.911955738256581

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
93.30730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-(benzoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240664
     RDKit          3D
Benzoylcarnitine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.4626   -1.4263    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514   -0.0696    1.1665 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4017    0.2467    2.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -0.0721    2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.8728    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    0.5506   -0.9223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1467    1.6659   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    1.5121   -3.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    0.5695   -3.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    2.4769   -4.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394    0.3938   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.7804   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.7373   -1.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.8503   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -1.9995   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.0017    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -0.8992    0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    0.2458    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623    0.2361    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.0266    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3029   -1.9356    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -1.3774   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7648   -0.6674    2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.0178    2.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.6064    1.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108    0.0303    3.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.7977    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967   -1.0266    1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636    0.9572   -0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    1.9024    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.3909   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    1.7122   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    2.6578   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903    3.2808   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -2.8547   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -2.9038    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994   -0.9447    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.0950    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.1364    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 10 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  CHG  1   2   1
M  END

HEADER    PROTEIN                                 05-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-20         0                                  
HETATM    1  C   UNK     0      -8.639  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.306  -1.143   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.973  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.641  -1.143   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.973   1.167   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -8.639   1.167   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -9.972   1.933   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0     -11.312   1.163   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.972   3.473   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.564   2.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.956  -1.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.956  -2.701   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.623  -3.473   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0     -11.289  -3.473   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.641  -2.683   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.307  -3.453   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.973  -2.684   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.973  -1.144   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.307  -0.373   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3   15   19                                                  
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   16    4                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0240664
HETATM    1  C1  UNL     1      -2.463  -1.426   0.720  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.251  -0.070   1.167  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -3.402   0.247   2.014  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.081  -0.072   2.014  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.075   0.873   0.125  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.056   0.551  -0.922  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.147   1.666  -1.957  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.202   1.512  -3.071  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.608   0.569  -3.176  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.216   2.477  -4.066  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.239   0.394  -0.447  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.943  -0.780  -0.595  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.387  -1.737  -1.178  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.298  -0.850  -0.066  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.065  -1.999  -0.179  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.337  -2.002   0.342  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.886  -0.899   0.976  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.134   0.246   1.093  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.862   0.236   0.569  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.530  -2.027   0.751  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.303  -1.936   1.240  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.774  -1.377  -0.344  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.765  -0.667   2.535  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.162   1.018   2.764  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.252   0.606   1.398  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.411   0.030   3.076  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.446   0.798   1.745  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.497  -1.027   1.894  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.064   0.957  -0.418  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.868   1.902   0.477  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.369  -0.391  -1.422  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.168   1.712  -2.399  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.940   2.658  -1.488  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.390   3.281  -4.082  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.624  -2.855  -0.677  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.961  -2.904   0.262  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.899  -0.945   1.374  1.00  0.00           H  
HETATM   38  H19 UNL     1       4.570   1.095   1.588  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.235   1.136   0.646  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    5
CONECT    3   23   24   25
CONECT    4   26   27   28
CONECT    5    6   29   30
CONECT    6    7   11   31
CONECT    7    8   32   33
CONECT    8    9    9   10
CONECT   10   34
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   39
END

HMDB0240664
     RDKit          3D
Benzoylcarnitine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.4626   -1.4263    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514   -0.0696    1.1665 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4017    0.2467    2.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -0.0721    2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.8728    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    0.5506   -0.9223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1467    1.6659   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    1.5121   -3.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    0.5695   -3.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    2.4769   -4.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394    0.3938   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.7804   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.7373   -1.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.8503   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -1.9995   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.0017    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -0.8992    0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    0.2458    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623    0.2361    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.0266    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3029   -1.9356    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -1.3774   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7648   -0.6674    2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.0178    2.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521    0.6064    1.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108    0.0303    3.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.7977    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967   -1.0266    1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636    0.9572   -0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    1.9024    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.3909   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678    1.7122   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    2.6578   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903    3.2808   -4.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -2.8547   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -2.9038    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994   -0.9447    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.0950    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    1.1364    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 10 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  CHG  1   2   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Benzoyl carnitine	HMDB
Benzoylcarnitine	HMDB

Chemical Formula

C₁₄H₂₀NO₄

Average Molecular Weight

266.316

Monoisotopic Molecular Weight

266.138684548

IUPAC Name

(3R)-3-(benzoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-(benzoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

105450-08-6

SMILES

C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H19NO4/c1-15(2,3)10-12(9-13(16)17)19-14(18)11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3/p+1/t12-/m1/s1

InChI Key

AWUHAZDZHNWQAG-GFCCVEGCSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240664)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-2.4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.31 m³·mol⁻¹	ChemAxon
Polarizability	27.77 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	161.585	30932474
DeepCCS	[M-H]-	159.227	30932474
DeepCCS	[M-2H]-	192.874	30932474
DeepCCS	[M+Na]+	168.101	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.05 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1809 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1031.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	212.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	342.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	816.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	879.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	146.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1326.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	359.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	324.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	63.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)C1=CC=CC=C1	2862.9	Standard polar	33892256
Benzoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)C1=CC=CC=C1	1828.7	Standard non polar	33892256
Benzoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)C1=CC=CC=C1	1942.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoylcarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@@H](CC(=O)O[Si](C)(C)C)OC(=O)C1=CC=CC=C1	1952.5	Semi standard non polar	33892256
Benzoylcarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[N+](C)(C)C)OC(=O)C1=CC=CC=C1	2212.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylcarnitine 10V, Positive-QTOF	splash10-014l-2790000000-6292d825b649662058d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylcarnitine 20V, Positive-QTOF	splash10-0btj-9800000000-1bea2cef004dfb0665b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylcarnitine 40V, Positive-QTOF	splash10-052r-9300000000-c83160bcfdf30fc87776	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

114314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129022

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
Sakuma T, Asai K, Ichiki T, Sugiyama N, Kidouchi K, Wada Y: Identification of benzoylcarnitine in the urine of a patient of hyperammonemia. Tohoku J Exp Med. 1989 Oct;159(2):147-51. doi: 10.1620/tjem.159.147. [PubMed:2609332 ]

Showing metabocard for Benzoylcarnitine (HMDB0240664)

MOL for HMDB0240664 (Benzoylcarnitine)

3D MOL for HMDB0240664 (Benzoylcarnitine)

3D SDF for HMDB0240664 (Benzoylcarnitine)

3D-SDF for HMDB0240664 (Benzoylcarnitine)

PDB for HMDB0240664 (Benzoylcarnitine)

3D PDB for HMDB0240664 (Benzoylcarnitine)

SMILES for HMDB0240664 (Benzoylcarnitine)

INCHI for HMDB0240664 (Benzoylcarnitine)

Structure for HMDB0240664 (Benzoylcarnitine)

3D Structure for HMDB0240664 (Benzoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra