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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:41:54 UTC

Update Date

2021-09-14 15:39:03 UTC

HMDB ID

HMDB0041836

Secondary Accession Numbers

HMDB41836

Metabolite Identification

Common Name

Benzoyl ecgonine

Description

Benzoyl ecgonine, also known as BCG or BEG, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Based on a literature review very few articles have been published on Benzoyl ecgonine.

Structure

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

HMDB0041836
     RDKit          3D
Benzoyl ecgonine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.5363   -1.2539   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.0812    0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.2429    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410    1.7724    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    2.2405    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    0.9309   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.4949   -0.8216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0416   -0.0554   -2.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.2124   -2.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    0.7924   -3.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -0.4374    0.1991 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7670   -0.2204    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -1.2076   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3372   -0.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -0.9106    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688    0.3443    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9119    0.6422    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -0.3377    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273   -1.5875   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -1.8648   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2944    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -1.4836   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.3705   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397   -2.0296    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -0.1430    2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    2.0569    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907    2.1073    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665    2.8929   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    2.7392    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995    1.0640   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.4246   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762    1.7951   -3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -1.4788   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607    1.1291    0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511    1.6316    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904   -0.0535    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1723   -2.3416   -0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410   -2.8537   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467   -1.2947    2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.3857    2.2079 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11 21  1  0
  6  2  1  0
 20 15  1  0
 21  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  6
 10 32  1  0
 11 33  1  6
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

  Mrv0541 06301311502D          

 22 24  0  0  0  0            999 V2000
    0.0773    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5997   -4.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0129   -3.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -4.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011   -2.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -3.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -2.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3311   -1.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630   -2.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -1.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7775   -1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -1.0800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 16 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 13 21  1  6  0  0  0
 21 16  1  0  0  0  0
 13 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041836

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11?,12?,13-,14-/m0/s1

> <INCHI_KEY>
GVGYEFKIHJTNQZ-HOAMVYINSA-N

> <FORMULA>
C16H19NO4

> <MOLECULAR_WEIGHT>
289.3264

> <EXACT_MASS>
289.131408101

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.235749297744007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
-0.5948680834280385

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.146437331171649

> <JCHEM_PKA_STRONGEST_BASIC>
9.54083420293863

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
76.39129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041836
     RDKit          3D
Benzoyl ecgonine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.5363   -1.2539   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.0812    0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.2429    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410    1.7724    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    2.2405    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    0.9309   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.4949   -0.8216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0416   -0.0554   -2.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.2124   -2.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    0.7924   -3.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -0.4374    0.1991 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7670   -0.2204    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -1.2076   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3372   -0.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -0.9106    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688    0.3443    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9119    0.6422    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -0.3377    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273   -1.5875   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -1.8648   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2944    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -1.4836   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.3705   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397   -2.0296    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -0.1430    2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    2.0569    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907    2.1073    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665    2.8929   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    2.7392    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995    1.0640   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.4246   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762    1.7951   -3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -1.4788   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607    1.1291    0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511    1.6316    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904   -0.0535    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1723   -2.3416   -0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410   -2.8537   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467   -1.2947    2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.3857    2.2079 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11 21  1  0
  6  2  1  0
 20 15  1  0
 21  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  6
 10 32  1  0
 11 33  1  6
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 30-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-13         0                                  
HETATM    1  C   UNK     0       0.144   1.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.586  -7.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.357  -6.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.046  -7.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.589  -5.209   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.277  -6.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.049  -5.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.008  -1.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.485  -3.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.280  -3.873   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.933  -0.219   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       3.478  -4.362   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.969  -3.457   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.051  -2.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.740  -3.871   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       5.421  -2.016   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   11   13                                                       
CONECT   10    5    6   16                                                  
CONECT   11    7    9   17                                                  
CONECT   12    8   14   17                                                  
CONECT   13    9   14   21   22                                             
CONECT   14   12   13   15                                                  
CONECT   15   14   18   19                                                  
CONECT   16   10   20   21                                                  
CONECT   17    1   11   12                                                  
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   13   16                                                       
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0041836
HETATM    1  C1  UNL     1      -3.536  -1.254  -0.125  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.348   0.081   0.305  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.658   0.243   1.547  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.541   1.772   1.620  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.614   2.241   0.186  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.624   0.931  -0.576  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.203   0.495  -0.822  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.042  -0.055  -2.195  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.681  -1.212  -2.470  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.317   0.792  -3.264  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.649  -0.437   0.199  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.767  -0.220   0.258  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.690  -1.208  -0.027  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.255  -2.337  -0.348  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.123  -0.911   0.053  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.569   0.344   0.409  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.912   0.642   0.489  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.846  -0.338   0.207  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.427  -1.587  -0.148  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.080  -1.865  -0.223  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.266  -0.294   1.573  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.640  -1.484  -0.048  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.323  -1.371  -1.227  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.040  -2.030   0.480  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.263  -0.143   2.402  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.577   2.057   2.101  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.391   2.107   2.224  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.766   2.893  -0.091  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.597   2.739   0.032  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.100   1.064  -1.571  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.558   1.425  -0.811  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.176   1.795  -3.191  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.780  -1.479  -0.113  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.861   1.129   0.635  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.251   1.632   0.770  1.00  0.00           H  
HETATM   36  H15 UNL     1       6.890  -0.054   0.284  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.172  -2.342  -0.366  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.741  -2.854  -0.503  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.247  -1.295   2.087  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.647   0.386   2.208  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    6
CONECT    3    4   21   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30
CONECT    7    8   11   31
CONECT    8    9    9   10
CONECT   10   32
CONECT   11   12   21   33
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16   20
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   38
CONECT   21   39   40
END

HMDB0041836
     RDKit          3D
Benzoyl ecgonine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.5363   -1.2539   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.0812    0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.2429    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410    1.7724    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    2.2405    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    0.9309   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    0.4949   -0.8216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0416   -0.0554   -2.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.2124   -2.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    0.7924   -3.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -0.4374    0.1991 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7670   -0.2204    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -1.2076   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3372   -0.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -0.9106    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688    0.3443    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9119    0.6422    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -0.3377    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273   -1.5875   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -1.8648   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2944    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -1.4836   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.3705   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397   -2.0296    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -0.1430    2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    2.0569    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907    2.1073    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665    2.8929   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    2.7392    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995    1.0640   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.4246   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762    1.7951   -3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -1.4788   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607    1.1291    0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511    1.6316    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904   -0.0535    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1723   -2.3416   -0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410   -2.8537   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467   -1.2947    2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.3857    2.2079 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11 21  1  0
  6  2  1  0
 20 15  1  0
 21  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  6
 10 32  1  0
 11 33  1  6
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Benzoylecgonine	HMDB
(1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB
3-(BENZOYLOXY)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylIC ACID	HMDB
BCG	HMDB
BEG	HMDB
Benzoylecgonine	HMDB
Benzoylecgonine hydrate	HMDB
Benzoylecgonine solution	HMDB
Benzoylecogonine	HMDB
Ecgonine benzoate	HMDB
O-Benzoyl-(-)-ecgonine	HMDB
O-Benzoylecgonine	HMDB
(2S,3S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	HMDB
Benzoylecgonine, (1R-(2-endo,3-exo))-isomer	HMDB
Benzoyl ecgonine	MeSH

Chemical Formula

C₁₆H₁₉NO₄

Average Molecular Weight

289.3264

Monoisotopic Molecular Weight

289.131408101

IUPAC Name

(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Traditional Name

(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

CAS Registry Number

519-09-5

SMILES

[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11?,12?,13-,14-/m0/s1

InChI Key

GVGYEFKIHJTNQZ-HOAMVYINSA-N

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
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0041836)

Organ

Liver (HMDB: HMDB0041836)
Kidney (HMDB: HMDB0041836)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0041836)

Cellular substructure

Cytoplasm (HMDB: HMDB0041836)

Source

Exogenous

Exogenous (HMDB: HMDB0041836)

Endogenous

Endogenous (HMDB: HMDB0041836)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °C	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
Water Solubility	3.82 g/L	ALOGPS
logP	1.71	ALOGPS
logP	-0.59	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.39 m³·mol⁻¹	ChemAxon
Polarizability	30.24 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	168.018	31661259
DarkChem	[M-H]-	163.474	31661259
DeepCCS	[M+H]+	166.152	30932474
DeepCCS	[M-H]-	163.794	30932474
DeepCCS	[M-2H]-	197.578	30932474
DeepCCS	[M+Na]+	172.763	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	172.3	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	169.0	32859911
AllCCS	[M+HCOO]-	168.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoyl ecgonine	[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1	3416.8	Standard polar	33892256
Benzoyl ecgonine	[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1	2519.7	Standard non polar	33892256
Benzoyl ecgonine	[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1	2353.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoyl ecgonine,1TMS,isomer #1	CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C)[C@@H](OC(=O)C1=CC=CC=C1)C2	2309.0	Semi standard non polar	33892256
Benzoyl ecgonine,1TBDMS,isomer #1	CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](OC(=O)C1=CC=CC=C1)C2	2541.8	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 - Benzoyl ecgonine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9300000000-2744be9f1b527a82cbd4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoyl ecgonine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4j-9610000000-67e335ee9149b74d3c8f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoyl ecgonine 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 - Benzoyl ecgonine 10V, Positive-QTOF	splash10-006x-0490000000-b318fb29702eb5424d35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 20V, Positive-QTOF	splash10-0ab9-0950000000-12bed261b67b5013666e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 40V, Positive-QTOF	splash10-0a4j-9800000000-3a17195c76e52677183c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 10V, Negative-QTOF	splash10-000f-0190000000-083b9c17aad363499aa7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 20V, Negative-QTOF	splash10-006x-1490000000-2fc324c6b5bed2c47666	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 40V, Negative-QTOF	splash10-00bi-3900000000-deb0d1b5a143fa9057b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 10V, Positive-QTOF	splash10-006x-0490000000-73dcb4693bdcc9d793a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 20V, Positive-QTOF	splash10-00di-0940000000-c6242975d7a936a067a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 40V, Positive-QTOF	splash10-059y-2910000000-f6eeecc6ba0155e0b530	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 10V, Negative-QTOF	splash10-00di-0490000000-ea962da37561e20e77d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 20V, Negative-QTOF	splash10-00b9-8920000000-186f5b09ff6d5345cb78	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyl ecgonine 40V, Negative-QTOF	splash10-004i-9210000000-af339a4c2382019d4d68	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

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

C00002280

Chemspider ID

220721

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442997

PDB ID

Not Available

ChEBI ID

41001

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

Not Available

Showing metabocard for Benzoyl ecgonine (HMDB0041836)

MOL for HMDB0041836 (Benzoyl ecgonine)

3D MOL for HMDB0041836 (Benzoyl ecgonine)

3D SDF for HMDB0041836 (Benzoyl ecgonine)

3D-SDF for HMDB0041836 (Benzoyl ecgonine)

PDB for HMDB0041836 (Benzoyl ecgonine)

3D PDB for HMDB0041836 (Benzoyl ecgonine)

SMILES for HMDB0041836 (Benzoyl ecgonine)

INCHI for HMDB0041836 (Benzoyl ecgonine)

Structure for HMDB0041836 (Benzoyl ecgonine)

3D Structure for HMDB0041836 (Benzoyl ecgonine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra