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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:49 UTC

Update Date

2021-09-14 15:45:57 UTC

HMDB ID

HMDB0041955

Secondary Accession Numbers

HMDB41955

Metabolite Identification

Common Name

Norcocaine

Description

Norcocaine belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Based on a literature review a significant number of articles have been published on Norcocaine.

Structure

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

HMDB0041955
     RDKit          3D
Norcocaine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5586    0.2361   -2.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510    0.0894   -1.6450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565    1.1050   -1.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    2.1788   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.9159   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    0.6029    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315    0.6816    2.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.6788    2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -1.4796    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.4747   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -0.1036   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941    0.2933   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3770    0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102   -0.5794   -0.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199   -0.2200   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -0.5736    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521   -0.2552    1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7058    0.4348    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860    0.8009   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801    0.4663   -1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709   -0.7595    1.0341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.4531   -2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1317   -0.0102   -3.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9504    1.2548   -2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.8813   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946    1.2686    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.5028    2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833    0.8083    3.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842   -0.5489    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -1.1447    3.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.5043    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047   -2.0457   -0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0580   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.1903   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0544   -1.1287    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377   -0.5533    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258    0.6727    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339    1.3468   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    0.7690   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -0.9540    1.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 11  5  1  0
 20 15  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

  Mrv0541 09131211492D          

 21 23  0  0  0  0            999 V2000
    0.2388   -2.6276    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
    1.0605   -0.5572    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
    2.1275   -1.3591    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
    1.6113   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 C   0  0  0  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
    0.4999   -0.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -2.7880    0.0000 O   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
    3.3643   -2.0748    0.0000 O   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  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041955

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1C2CCC(CC1C(=O)OC1=CC=CC=C1)N2

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

> <INCHI_KEY>
RERBBBLSJAMJFJ-UHFFFAOYSA-N

> <FORMULA>
C16H19NO4

> <MOLECULAR_WEIGHT>
289.3264

> <EXACT_MASS>
289.131408101

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.17523785833214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl 3-phenyl 8-azabicyclo[3.2.1]octane-2,3-dicarboxylate

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.7339623140000002

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.558750871497276

> <JCHEM_POLAR_SURFACE_AREA>
64.63000000000001

> <JCHEM_REFRACTIVITY>
75.3584

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norcocaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041955
     RDKit          3D
Norcocaine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5586    0.2361   -2.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510    0.0894   -1.6450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565    1.1050   -1.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    2.1788   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.9159   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    0.6029    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315    0.6816    2.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.6788    2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -1.4796    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.4747   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -0.1036   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941    0.2933   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3770    0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102   -0.5794   -0.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199   -0.2200   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -0.5736    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521   -0.2552    1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7058    0.4348    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860    0.8009   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801    0.4663   -1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709   -0.7595    1.0341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.4531   -2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1317   -0.0102   -3.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9504    1.2548   -2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.8813   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946    1.2686    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.5028    2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833    0.8083    3.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842   -0.5489    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -1.1447    3.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.5043    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047   -2.0457   -0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0580   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.1903   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0544   -1.1287    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377   -0.5533    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258    0.6727    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339    1.3468   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    0.7690   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -0.9540    1.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 11  5  1  0
 20 15  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       0.446  -4.905   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       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.049  -5.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.194  -1.737   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       4.740  -3.871   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.485  -3.185   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       3.969  -5.204   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.478  -4.362   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.969  -3.457   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.280  -3.873   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   10                                                       
CONECT    8    7   13                                                       
CONECT    9   10   12                                                       
CONECT   10    7    9   17                                                  
CONECT   11    5    6   21                                                  
CONECT   12    9   14   15                                                  
CONECT   13    8   14   17                                                  
CONECT   14   12   13   16                                                  
CONECT   15   12   18   21                                                  
CONECT   16   14   19   20                                                  
CONECT   17   10   13                                                       
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    1   16                                                       
CONECT   21   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0041955
HETATM    1  C1  UNL     1      -4.559   0.236  -2.629  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.551   0.089  -1.645  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.657   1.105  -1.319  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.765   2.179  -1.930  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.606   0.916  -0.276  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.313   0.603   1.013  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.432   0.682   2.219  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.758  -0.679   2.228  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.512  -1.480   1.203  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.842  -1.475  -0.145  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.610  -0.104  -0.695  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.794   0.293  -0.413  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.127   1.377   0.125  1.00  0.00           O  
HETATM   14  O4  UNL     1       1.810  -0.579  -0.761  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.120  -0.220  -0.503  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.653  -0.574   0.710  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.952  -0.255   1.050  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.706   0.435   0.128  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.186   0.801  -1.101  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.880   0.466  -1.411  1.00  0.00           C  
HETATM   21  N1  UNL     1      -2.771  -0.760   1.034  1.00  0.00           N  
HETATM   22  H1  UNL     1      -5.413  -0.453  -2.381  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.132  -0.010  -3.618  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.950   1.255  -2.571  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.079   1.881  -0.133  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.195   1.269   1.099  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.693   1.503   2.185  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.083   0.808   3.127  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.284  -0.549   1.912  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.779  -1.145   3.235  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.731  -2.504   1.497  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.505  -2.046  -0.837  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.099  -2.058  -0.071  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.674  -0.190  -1.820  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.054  -1.129   1.457  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.338  -0.553   2.020  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.726   0.673   0.422  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.834   1.347  -1.788  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.500   0.769  -2.387  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.456  -0.954   1.768  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   11   25
CONECT    6    7   21   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   21   31
CONECT   10   11   32   33
CONECT   11   12   34
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   39
CONECT   21   40
END

HMDB0041955
     RDKit          3D
Norcocaine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5586    0.2361   -2.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510    0.0894   -1.6450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565    1.1050   -1.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    2.1788   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.9159   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    0.6029    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315    0.6816    2.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.6788    2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -1.4796    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.4747   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -0.1036   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941    0.2933   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3770    0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102   -0.5794   -0.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199   -0.2200   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -0.5736    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521   -0.2552    1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7058    0.4348    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860    0.8009   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801    0.4663   -1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709   -0.7595    1.0341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4126   -0.4531   -2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1317   -0.0102   -3.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9504    1.2548   -2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.8813   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946    1.2686    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.5028    2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833    0.8083    3.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842   -0.5489    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -1.1447    3.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.5043    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047   -2.0457   -0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0580   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.1903   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0544   -1.1287    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377   -0.5533    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258    0.6727    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339    1.3468   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    0.7690   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -0.9540    1.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 11  5  1  0
 20 15  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl 3-phenyl 8-azabicyclo[3.2.1]octane-2,3-dicarboxylic acid	HMDB

Chemical Formula

C₁₆H₁₉NO₄

Average Molecular Weight

289.3264

Monoisotopic Molecular Weight

289.131408101

IUPAC Name

2-methyl 3-phenyl 8-azabicyclo[3.2.1]octane-2,3-dicarboxylate

Traditional Name

norcocaine

CAS Registry Number

18717-72-1

SMILES

COC(=O)C1C2CCC(CC1C(=O)OC1=CC=CC=C1)N2

InChI Identifier

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

InChI Key

RERBBBLSJAMJFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Piperidinecarboxylic acid
Tropane alkaloid
Phenoxy compound
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Pyrrolidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Secondary aliphatic amine
Carboxylic acid derivative
Secondary amine
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041955)

Source

Endogenous

Endogenous (HMDB: HMDB0041955)

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
Water Solubility	0.49 g/L	ALOGPS
logP	0.83	ALOGPS
logP	1.73	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	9.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.36 m³·mol⁻¹	ChemAxon
Polarizability	30.18 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	168.696	31661259
DarkChem	[M-H]-	166.302	31661259
DeepCCS	[M+H]+	164.378	30932474
DeepCCS	[M-H]-	162.02	30932474
DeepCCS	[M-2H]-	194.931	30932474
DeepCCS	[M+Na]+	170.471	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.6	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norcocaine	COC(=O)C1C2CCC(CC1C(=O)OC1=CC=CC=C1)N2	3202.4	Standard polar	33892256
Norcocaine	COC(=O)C1C2CCC(CC1C(=O)OC1=CC=CC=C1)N2	2297.5	Standard non polar	33892256
Norcocaine	COC(=O)C1C2CCC(CC1C(=O)OC1=CC=CC=C1)N2	2312.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norcocaine,1TMS,isomer #1	COC(=O)C1C(C(=O)OC2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C	2285.7	Semi standard non polar	33892256
Norcocaine,1TMS,isomer #1	COC(=O)C1C(C(=O)OC2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C	2251.0	Standard non polar	33892256
Norcocaine,1TBDMS,isomer #1	COC(=O)C1C(C(=O)OC2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C(C)(C)C	2517.0	Semi standard non polar	33892256
Norcocaine,1TBDMS,isomer #1	COC(=O)C1C(C(=O)OC2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C(C)(C)C	2454.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norcocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l7-9420000000-4b4d8376f2b4cd093f05	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcocaine 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 - Norcocaine 10V, Positive-QTOF	splash10-0006-0290000000-b6128cca848d5e04cab7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 20V, Positive-QTOF	splash10-0005-2950000000-dcc0d2435b9cbfaab3c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 40V, Positive-QTOF	splash10-052r-3900000000-8a2b7feb0ba5a5cbd0d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 10V, Negative-QTOF	splash10-000i-0090000000-00a726f89aaa3517380b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 20V, Negative-QTOF	splash10-0019-3390000000-cb1d25830e7b745ea65e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 40V, Negative-QTOF	splash10-0006-9500000000-374b03cfafa1accdd9cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 10V, Positive-QTOF	splash10-0006-0190000000-a4d3c18b7e995be5bdde	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 20V, Positive-QTOF	splash10-0a5l-0960000000-c94cf56854476ca6fe2e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 40V, Positive-QTOF	splash10-0bvj-4790000000-97c5d266e08fd987181c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 10V, Negative-QTOF	splash10-000i-0190000000-2b0cd0a06a321150247c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 20V, Negative-QTOF	splash10-05n0-2960000000-5240467e83b268e27a6a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaine 40V, Negative-QTOF	splash10-06r6-6980000000-e09def17831b93d85abf	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

Chemspider ID

27185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norcocaine

METLIN ID

Not Available

PubChem Compound

29230

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

Not Available

Showing metabocard for Norcocaine (HMDB0041955)

MOL for HMDB0041955 (Norcocaine)

3D MOL for HMDB0041955 (Norcocaine)

3D SDF for HMDB0041955 (Norcocaine)

3D-SDF for HMDB0041955 (Norcocaine)

PDB for HMDB0041955 (Norcocaine)

3D PDB for HMDB0041955 (Norcocaine)

SMILES for HMDB0041955 (Norcocaine)

INCHI for HMDB0041955 (Norcocaine)

Structure for HMDB0041955 (Norcocaine)

3D Structure for HMDB0041955 (Norcocaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra