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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:28 UTC

Update Date

2021-10-13 08:37:16 UTC

HMDB ID

HMDB0041860

Secondary Accession Numbers

HMDB41860

Metabolite Identification

Common Name

Cocaethylene

Description

Cocaethylene is a recreational drug with stimulant, euphoriant, anorectic, sympathomimetic and local anesthetic properties. Three monoamine neurotransmitters known as serotonin (5-HT), norepinephrine (NE), and dopamine (DA) play an important role in cocaethylene's action. Cocaethylene increases the level of serotonergic, noradrenergic, and dopaminergic neurotransmission by inhibiting the action of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) which makes cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).[Note 1]; Normally cocaine's metabolism produces two major and biologically inactive metabolites, benzoylecogonine and ecgonine methyl ester. Carboxylesterase is an important part of cocaine's metabolism because it acts as the catalyst for the hydrolysis of cocaine which produces the inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, instead of undergoing hydrolysis with water, which results in cocaethylene.

Structure

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

HMDB0041860
     RDKit          3D
Cocaethylene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.0374    4.0309    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013    3.4716   -0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    2.3609   -0.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    1.1780   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2406    1.2006   -0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.0732    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3242   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -0.2439   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106    0.6705   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.4379   -1.5644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.7241   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3991    1.6312   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003    1.6824   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973    0.8246    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827   -0.0840    1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.1302    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -1.6123   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.6623   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2027    0.4769   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810    2.3059   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932    2.3900   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2157   -0.8540    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -2.0112   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -1.4093   -2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214   -3.5847   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179   -3.7721   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -3.0408   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -1.8684    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.9022   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4772   -0.9080    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6728   -3.1796    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -3.2251    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -4.2485    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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M  END


  Mrv0541 09131211442D          

 23 25  0  0  0  0            999 V2000
   -0.5733   -2.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0773    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388   -2.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039    0.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -0.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3657   -0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.3615    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
    3.7775   -1.3607    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
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    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
    3.7761   -2.7897    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
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
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  8  6  2  0  0  0  0
 10  9  1  0  0  0  0
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 22 18  1  0  0  0  0
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 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041860

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3

> <INCHI_KEY>
NMPOSNRHZIWLLL-UHFFFAOYSA-N

> <FORMULA>
C18H23NO4

> <MOLECULAR_WEIGHT>
317.3795

> <EXACT_MASS>
317.162708229

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.98370549474803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.6389159636666655

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.771445331978661

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
85.90899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041860
     RDKit          3D
Cocaethylene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.0374    4.0309    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013    3.4716   -0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    2.3609   -0.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    1.1780   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2406    1.2006   -0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.0732    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3242   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -0.2439   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106    0.6705   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.4379   -1.5644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.7241   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3991    1.6312   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003    1.6824   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973    0.8246    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827   -0.0840    1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.1302    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -1.6123   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.6623   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991   -2.8914   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -1.5850   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -1.1062    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -2.2179    0.9511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721   -3.2748    1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    3.7688    1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    5.1488   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    3.7188   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    4.2607   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6881    3.2578   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918    0.3938    1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.4769   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810    2.3059   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932    2.3900   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1150    0.8851    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094   -0.7564    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -0.8540    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -2.0112   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -1.4093   -2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214   -3.5847   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179   -3.7721   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -3.0408   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -1.8684    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.9022   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4772   -0.9080    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6728   -3.1796    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -3.2251    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -4.2485    1.2507 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  2  0
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 13 14  2  0
 14 15  1  0
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  7 17  1  0
 17 18  1  0
 18 19  1  0
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 20 21  1  0
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 22 23  1  0
 21  6  1  0
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 22 18  1  0
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 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  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      -1.070  -5.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.144   1.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.446  -4.905   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.594   0.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.054   0.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.363  -1.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.283  -1.205   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.591  -2.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.051  -2.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.008  -1.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.280  -3.873   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.485  -3.185   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.933  -0.219   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       7.049  -5.207   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.478  -4.362   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.969  -3.457   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.740  -3.871   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   19                                                            
CONECT    3    1   22                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9   10   13                                                       
CONECT   10    9   14                                                       
CONECT   11   13   15                                                       
CONECT   12    7    8   17                                                  
CONECT   13    9   11   19                                                  
CONECT   14   10   16   19                                                  
CONECT   15   11   16   23                                                  
CONECT   16   14   15   18                                                  
CONECT   17   12   20   23                                                  
CONECT   18   16   21   22                                                  
CONECT   19    2   13   14                                                  
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22    3   18                                                       
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0041860
HETATM    1  C1  UNL     1      -3.037   4.031   0.089  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.101   3.472  -0.938  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.366   2.361  -0.492  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.998   1.178  -0.062  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.241   1.201  -0.111  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.142   0.073   0.387  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.141  -0.324  -0.670  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.187  -0.244  -0.176  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.111   0.671  -0.660  1.00  0.00           C  
HETATM   10  O4  UNL     1       1.727   1.438  -1.564  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.484   0.724  -0.122  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.399   1.631  -0.602  1.00  0.00           C  
HETATM   13  C9  UNL     1       5.700   1.682  -0.092  1.00  0.00           C  
HETATM   14  C10 UNL     1       6.097   0.825   0.905  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.183  -0.084   1.387  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.893  -0.130   0.877  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.418  -1.612  -1.362  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.919  -2.662  -0.435  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.399  -2.891  -0.740  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.971  -1.585  -0.190  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.969  -1.106   0.794  1.00  0.00           C  
HETATM   22  N1  UNL     1      -1.016  -2.218   0.951  1.00  0.00           N  
HETATM   23  C18 UNL     1      -1.572  -3.275   1.747  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.676   3.769   1.090  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.058   5.149  -0.001  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.106   3.719  -0.080  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.369   4.261  -1.205  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.688   3.258  -1.854  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.592   0.394   1.334  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.203   0.477  -1.468  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.081   2.306  -1.389  1.00  0.00           H  
HETATM   32  H9  UNL     1       6.393   2.390  -0.476  1.00  0.00           H  
HETATM   33  H10 UNL     1       7.115   0.885   1.284  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.509  -0.756   2.175  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.216  -0.854   1.283  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.467  -2.011  -1.906  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.203  -1.409  -2.141  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.321  -3.585  -0.537  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.718  -3.772  -0.160  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.601  -3.041  -1.802  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.926  -1.868   0.336  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.250  -0.902  -0.993  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.477  -0.908   1.777  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.673  -3.180   1.812  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.087  -3.225   2.747  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.323  -4.248   1.251  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   21   29
CONECT    7    8   17   30
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   35
CONECT   17   18   36   37
CONECT   18   19   22   38
CONECT   19   20   39   40
CONECT   20   21   41   42
CONECT   21   22   43
CONECT   22   23
CONECT   23   44   45   46
END

HMDB0041860
     RDKit          3D
Cocaethylene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.0374    4.0309    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013    3.4716   -0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    2.3609   -0.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    1.1780   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2406    1.2006   -0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.0732    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3242   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -0.2439   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106    0.6705   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.4379   -1.5644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.7241   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3991    1.6312   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003    1.6824   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973    0.8246    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827   -0.0840    1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.1302    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -1.6123   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.6623   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991   -2.8914   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -1.5850   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -1.1062    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -2.2179    0.9511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721   -3.2748    1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    3.7688    1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    5.1488   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    3.7188   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    4.2607   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6881    3.2578   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918    0.3938    1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.4769   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810    2.3059   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932    2.3900   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1150    0.8851    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094   -0.7564    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -0.8540    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -2.0112   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -1.4093   -2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214   -3.5847   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179   -3.7721   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -3.0408   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -1.8684    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.9022   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4772   -0.9080    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6728   -3.1796    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -3.2251    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -4.2485    1.2507 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21  6  1  0
 16 11  1  0
 22 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethylbenzoylecgonine	HMDB
Homocaine	HMDB
Thylbenzoylecgonine (cocaethylene)	HMDB
Coca-ethylene	HMDB
Benzoylecgonine ethyl ester	HMDB
Ethylcocaine	HMDB
Ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB

Chemical Formula

C₁₈H₂₃NO₄

Average Molecular Weight

317.3795

Monoisotopic Molecular Weight

317.162708229

IUPAC Name

ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

CAS Registry Number

529-38-4

SMILES

CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C

InChI Identifier

InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3

InChI Key

NMPOSNRHZIWLLL-UHFFFAOYSA-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
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	349.92 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.404 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.16 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.64	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.91 m³·mol⁻¹	ChemAxon
Polarizability	33.98 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.418	31661259
DarkChem	[M-H]-	172.276	31661259
DeepCCS	[M+H]+	173.786	30932474
DeepCCS	[M-H]-	171.428	30932474
DeepCCS	[M-2H]-	204.949	30932474
DeepCCS	[M+Na]+	180.2	30932474
AllCCS	[M+H]+	177.7	32859911
AllCCS	[M+H-H2O]+	174.6	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.3	32859911
AllCCS	[M-H]-	176.6	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	176.8	32859911

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.	6.1 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2866 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	82.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1890.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	212.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	393.2 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	441.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	259.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	981.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	397.9 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	1322.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	288.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.8 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	66.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C	3114.7	Standard polar	33892256
Cocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C	2405.5	Standard non polar	33892256
Cocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C	2358.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

Not Available

Chemspider ID

2723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cocaethylene

METLIN ID

Not Available

PubChem Compound

2825

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1488541

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cocaethylene (HMDB0041860)

MOL for HMDB0041860 (Cocaethylene)

3D MOL for HMDB0041860 (Cocaethylene)

3D SDF for HMDB0041860 (Cocaethylene)

3D-SDF for HMDB0041860 (Cocaethylene)

PDB for HMDB0041860 (Cocaethylene)

3D PDB for HMDB0041860 (Cocaethylene)

SMILES for HMDB0041860 (Cocaethylene)

INCHI for HMDB0041860 (Cocaethylene)

Structure for HMDB0041860 (Cocaethylene)

3D Structure for HMDB0041860 (Cocaethylene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized