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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:32:29 UTC

Update Date

2021-09-26 23:10:49 UTC

HMDB ID

HMDB0255728

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Norcocaethylene

Description

ethyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate 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 ethyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Norcocaethylene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Norcocaethylene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255728
     RDKit          3D
Norcocaethylene
 43 45  0  0  0  0  0  0  0  0999 V2000
   -1.2228    3.7984   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.9371   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837    1.7790   -0.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8505   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    1.0461   -0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -0.3114    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.1659    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055   -1.5152   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6597   -3.0301   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890   -3.1474    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -2.4007   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.1741    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.4916    0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.4140    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -0.9582    2.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    0.2685    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949    0.3254    1.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990    0.9828    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285    1.5803    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163    1.5412   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2281    0.8726   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -2.4230    1.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124    3.8326   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    3.3221    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    4.8521   -0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462    2.6505   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170    3.5380   -0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.0715    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.6401    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307   -1.0014   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -1.3063   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -3.3436   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914   -3.5556   -0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473   -4.1841    0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -3.0615    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -2.1233   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.5628    1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770   -0.1509    2.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.9955    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498    2.0831    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706    2.0215   -1.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.8752   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -2.2629    1.9074 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10 22  1  0
 12  6  1  0
 21 16  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
M  END

  Mrv1652306031607372D          

 22 24  0  0  0  0            999 V2000
    2.0695    3.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    2.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265   -2.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890   -2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -1.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265   -1.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -0.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579    1.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075    0.0092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640   -0.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737    1.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565    2.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  2  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255728

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-2-21-17(20)15-13-9-8-12(18-13)10-14(15)22-16(19)11-6-4-3-5-7-11/h3-7,12-15,18H,2,8-10H2,1H3

> <INCHI_KEY>
MABVIZVTLRQVOB-UHFFFAOYSA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.358

> <EXACT_MASS>
303.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.997032462238028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
2.2558680263333324

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.96407328825756

> <JCHEM_POLAR_SURFACE_AREA>
64.63000000000001

> <JCHEM_REFRACTIVITY>
80.61429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255728
     RDKit          3D
Norcocaethylene
 43 45  0  0  0  0  0  0  0  0999 V2000
   -1.2228    3.7984   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.9371   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837    1.7790   -0.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8505   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    1.0461   -0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -0.3114    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.1659    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055   -1.5152   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6597   -3.0301   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890   -3.1474    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -2.4007   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.1741    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.4916    0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.4140    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -0.9582    2.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    0.2685    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949    0.3254    1.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990    0.9828    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285    1.5803    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163    1.5412   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2281    0.8726   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -2.4230    1.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124    3.8326   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    3.3221    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    4.8521   -0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462    2.6505   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170    3.5380   -0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.0715    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.6401    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307   -1.0014   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -1.3063   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -3.3436   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914   -3.5556   -0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473   -4.1841    0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -3.0615    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -2.1233   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.5628    1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770   -0.1509    2.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.9955    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498    2.0831    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706    2.0215   -1.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.8752   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -2.2629    1.9074 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10 22  1  0
 12  6  1  0
 21 16  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       3.863   6.680   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.426   5.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.736  -5.318   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.276  -5.318   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.966  -3.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.046  -3.984   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.736  -2.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.363  -0.753   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.363   0.787   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.068  -1.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.276  -2.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.567  -1.713   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.567   1.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.736   0.017   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.068   1.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.046  -1.317   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.028   2.609   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.134   0.017   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       7.586  -1.317   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.551   2.379   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.466   4.042   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.276   0.017   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   21                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10   12   14                                                       
CONECT   11    6    7   16                                                  
CONECT   12    8   10   18                                                  
CONECT   13    9   15   18                                                  
CONECT   14   10   15   22                                                  
CONECT   15   13   14   17                                                  
CONECT   16   11   19   22                                                  
CONECT   17   15   20   21                                                  
CONECT   18   12   13                                                       
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21    2   17                                                       
CONECT   22   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0255728
HETATM    1  C1  UNL     1      -1.223   3.798  -0.788  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.410   2.937  -1.161  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.484   1.779  -0.321  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.472   0.851  -0.258  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.455   1.046  -0.971  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.626  -0.311   0.631  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.828  -1.166   0.285  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.906  -1.515  -1.166  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.660  -3.030  -1.184  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.789  -3.147   0.076  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.526  -2.401  -0.200  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.396  -1.174   0.697  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.775  -0.492   0.322  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.831  -0.414   1.217  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.716  -0.958   2.347  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.073   0.268   0.916  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.095   0.325   1.823  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.299   0.983   1.541  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.428   1.580   0.304  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.416   1.541  -0.634  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.228   0.873  -0.310  1.00  0.00           C  
HETATM   22  N1  UNL     1      -2.660  -2.423   1.016  1.00  0.00           N  
HETATM   23  H1  UNL     1      -0.512   3.833  -1.642  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.722   3.322   0.072  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.520   4.852  -0.574  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.346   2.650  -2.224  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.317   3.538  -0.941  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.816   0.072   1.670  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.750  -0.640   0.603  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.131  -1.001  -1.781  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.898  -1.306  -1.625  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.133  -3.344  -2.083  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.591  -3.556  -0.962  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.647  -4.184   0.380  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.336  -3.061   0.049  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.392  -2.123  -1.272  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.261  -1.563   1.723  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.977  -0.151   2.794  1.00  0.00           H  
HETATM   39  H17 UNL     1       6.073   0.996   2.297  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.350   2.083   0.088  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.571   2.022  -1.578  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.472   0.875  -1.084  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.170  -2.263   1.907  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   12   28
CONECT    7    8   22   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   22   34
CONECT   11   12   35   36
CONECT   12   13   37
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17   21
CONECT   17   18   38
CONECT   18   19   19   39
CONECT   19   20   40
CONECT   20   21   21   41
CONECT   21   42
CONECT   22   43
END

HMDB0255728
     RDKit          3D
Norcocaethylene
 43 45  0  0  0  0  0  0  0  0999 V2000
   -1.2228    3.7984   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.9371   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837    1.7790   -0.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8505   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    1.0461   -0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -0.3114    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.1659    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055   -1.5152   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6597   -3.0301   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890   -3.1474    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -2.4007   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.1741    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.4916    0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.4140    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -0.9582    2.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    0.2685    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949    0.3254    1.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990    0.9828    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285    1.5803    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163    1.5412   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2281    0.8726   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -2.4230    1.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124    3.8326   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    3.3221    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    4.8521   -0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462    2.6505   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170    3.5380   -0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.0715    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.6401    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307   -1.0014   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -1.3063   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -3.3436   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914   -3.5556   -0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473   -4.1841    0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -3.0615    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -2.1233   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.5628    1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770   -0.1509    2.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.9955    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498    2.0831    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706    2.0215   -1.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.8752   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -2.2629    1.9074 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10 22  1  0
 12  6  1  0
 21 16  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid	Generator

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.358

Monoisotopic Molecular Weight

303.14705816

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2

InChI Identifier

InChI=1S/C17H21NO4/c1-2-21-17(20)15-13-9-8-12(18-13)10-14(15)22-16(19)11-6-4-3-5-7-11/h3-7,12-15,18H,2,8-10H2,1H3

InChI Key

MABVIZVTLRQVOB-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
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen 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 (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.93	ALOGPS
logP	2.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	9.96	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	6	ChemAxon
Refractivity	80.61 m³·mol⁻¹	ChemAxon
Polarizability	32 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
DeepCCS	[M+H]+	172.906	30932474
DeepCCS	[M-H]-	170.548	30932474
DeepCCS	[M-2H]-	203.434	30932474
DeepCCS	[M+Na]+	179.0	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.7	32859911
AllCCS	[M+NH4]+	175.7	32859911
AllCCS	[M+Na]+	176.5	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.5	32859911
AllCCS	[M+HCOO]-	172.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norcocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2	3244.1	Standard polar	33892256
Norcocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2	2411.5	Standard non polar	33892256
Norcocaethylene	CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2	2387.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norcocaethylene,1TMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C	2360.6	Semi standard non polar	33892256
Norcocaethylene,1TMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C	2331.5	Standard non polar	33892256
Norcocaethylene,1TMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C	3249.3	Standard polar	33892256
Norcocaethylene,1TBDMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C(C)(C)C	2591.1	Semi standard non polar	33892256
Norcocaethylene,1TBDMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C(C)(C)C	2526.2	Standard non polar	33892256
Norcocaethylene,1TBDMS,isomer #1	CCOC(=O)C1C(OC(=O)C2=CC=CC=C2)CC2CCC1N2[Si](C)(C)C(C)(C)C	3350.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norcocaethylene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-8930000000-e5e0d24eace75f501d86	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcocaethylene 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 - Norcocaethylene 10V, Positive-QTOF	splash10-0zfr-0659000000-80df110ec0a81225a3b9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaethylene 20V, Positive-QTOF	splash10-0a4i-0931000000-3591117da44d52c8ba83	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaethylene 40V, Positive-QTOF	splash10-0a4i-6900000000-c368c720b425077f57bc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaethylene 10V, Negative-QTOF	splash10-0udi-1169000000-1d85342debd243881e6f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaethylene 20V, Negative-QTOF	splash10-0kji-4893000000-b7394037a324dbc9057e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcocaethylene 40V, Negative-QTOF	splash10-00fr-4910000000-f475e0d7d932ee5c98d2	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

19981290

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21120676

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Norcocaethylene (HMDB0255728)

MOL for HMDB0255728 (Norcocaethylene)

3D MOL for HMDB0255728 (Norcocaethylene)

3D SDF for HMDB0255728 (Norcocaethylene)

3D-SDF for HMDB0255728 (Norcocaethylene)

PDB for HMDB0255728 (Norcocaethylene)

3D PDB for HMDB0255728 (Norcocaethylene)

SMILES for HMDB0255728 (Norcocaethylene)

INCHI for HMDB0255728 (Norcocaethylene)

Structure for HMDB0255728 (Norcocaethylene)

3D Structure for HMDB0255728 (Norcocaethylene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra