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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:07:01 UTC

Update Date

2022-11-23 22:06:02 UTC

HMDB ID

HMDB0251685

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ethyl ecgonine

Description

ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl ecgonine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl ecgonine 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

HMDB0251685
     RDKit          3D
Ecgonine Ethyl Ester
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4447   -0.3393    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -0.4962   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    0.1802   -0.9599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -0.2001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.1304    0.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954    0.5071   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033    0.3114   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.0806   -1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251    0.8122   -1.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    0.2643   -0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    1.3426    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.1743    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0220    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7281   -0.7552    0.0055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -1.5615    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -1.3496    0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722    0.0839    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    0.3231    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895   -1.5628   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    0.0040   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    1.5728   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    0.7657   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544   -1.5277   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    1.8957   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9876    0.3824   -2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4126   -0.1178   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295    1.1324    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    2.3336   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953    1.0138    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385    2.0814    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.6163    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.5808    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.2416    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -2.5988    0.8258 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
  7  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  1  0
 13  6  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  END


  Mrv1652306031607372D          

 15 16  0  0  0  0            999 V2000
    0.7393    3.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0408    2.2884    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
    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
    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
    2.8265    0.0092    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
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15  3  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251685

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1C2CCC(CC1O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO3/c1-3-15-11(14)10-8-5-4-7(12(8)2)6-9(10)13/h7-10,13H,3-6H2,1-2H3

> <INCHI_KEY>
ABDMBNAKYBUEEX-UHFFFAOYSA-N

> <FORMULA>
C11H19NO3

> <MOLECULAR_WEIGHT>
213.277

> <EXACT_MASS>
213.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.156438433969342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.14361611499999943

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.595394386142516

> <JCHEM_PKA_STRONGEST_BASIC>
8.914048749188986

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
56.08700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251685
     RDKit          3D
Ecgonine Ethyl Ester
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4447   -0.3393    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -0.4962   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    0.1802   -0.9599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -0.2001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.1304    0.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954    0.5071   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033    0.3114   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.0806   -1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251    0.8122   -1.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    0.2643   -0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    1.3426    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.1743    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0220    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7281   -0.7552    0.0055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -1.5615    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -1.3496    0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722    0.0839    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    0.3231    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895   -1.5628   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    0.0040   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    1.5728   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    0.7657   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544   -1.5277   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    1.8957   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9876    0.3824   -2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4126   -0.1178   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295    1.1324    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    2.3336   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953    1.0138    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385    2.0814    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.6163    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.5808    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.2416    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -2.5988    0.8258 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
  7  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  1  0
 13  6  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  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       1.380   5.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.406   0.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.943   4.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.363  -0.753   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.363   0.787   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.068  -1.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.567  -1.713   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.567   1.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.736   0.017   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.068   1.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.028   2.609   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.134   0.017   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.276   0.017   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.551   2.379   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.466   4.042   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1   15                                                       
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    4    6   12                                                  
CONECT    8    5   10   12                                                  
CONECT    9    6   10   13                                                  
CONECT   10    8    9   11                                                  
CONECT   11   10   14   15                                                  
CONECT   12    2    7    8                                                  
CONECT   13    9                                                            
CONECT   14   11                                                            
CONECT   15    3   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0251685
HETATM    1  C1  UNL     1       4.445  -0.339   0.520  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.899  -0.496  -0.858  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.642   0.180  -0.960  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.610  -0.200  -0.146  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.748  -1.130   0.687  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.295   0.507  -0.251  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.203   0.311  -1.671  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.256  -1.081  -1.870  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.625   0.812  -1.829  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.467   0.264  -0.704  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.674   1.343   0.342  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.500   1.174   1.271  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.714  -0.022   0.720  1.00  0.00           C  
HETATM   14  N1  UNL     1      -1.728  -0.755   0.006  1.00  0.00           N  
HETATM   15  C11 UNL     1      -2.555  -1.562   0.857  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.731  -1.350   0.905  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.672   0.084   1.219  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.327   0.323   0.485  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.789  -1.563  -1.167  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.562   0.004  -1.592  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.503   1.573  -0.027  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.460   0.766  -2.413  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.554  -1.528  -1.554  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.687   1.896  -1.937  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.988   0.382  -2.808  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.413  -0.118  -1.118  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.630   1.132   0.870  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.662   2.334  -0.132  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.795   1.014   2.308  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.839   2.081   1.212  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.275  -0.616   1.536  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.573  -1.581   0.472  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.493  -1.242   1.923  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.161  -2.599   0.826  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   13   21
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   24   25
CONECT   10   11   14   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   31
CONECT   14   15
CONECT   15   32   33   34
END

HMDB0251685
     RDKit          3D
Ecgonine Ethyl Ester
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.4447   -0.3393    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -0.4962   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    0.1802   -0.9599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -0.2001   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.1304    0.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954    0.5071   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033    0.3114   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.0806   -1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251    0.8122   -1.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    0.2643   -0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    1.3426    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.1743    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0220    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7281   -0.7552    0.0055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -1.5615    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -1.3496    0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722    0.0839    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    0.3231    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895   -1.5628   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    0.0040   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    1.5728   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    0.7657   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544   -1.5277   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    1.8957   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9876    0.3824   -2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4126   -0.1178   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295    1.1324    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    2.3336   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953    1.0138    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385    2.0814    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.6163    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.5808    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.2416    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -2.5988    0.8258 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
  7  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  1  0
 13  6  1  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₉NO₃

Average Molecular Weight

213.277

Monoisotopic Molecular Weight

213.136493476

IUPAC Name

ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

ethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1C2CCC(CC1O)N2C

InChI Identifier

InChI=1S/C11H19NO3/c1-3-15-11(14)10-8-5-4-7(12(8)2)6-9(10)13/h7-10,13H,3-6H2,1-2H3

InChI Key

ABDMBNAKYBUEEX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Piperidinecarboxylic acid
Tropane alkaloid
Beta-hydroxy acid
Hydroxy acid
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Alcohol
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	0.58	ALOGPS
logP	0.14	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.09 m³·mol⁻¹	ChemAxon
Polarizability	23.16 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	151.196	30932474
DeepCCS	[M-H]-	148.821	30932474
DeepCCS	[M-2H]-	183.847	30932474
DeepCCS	[M+Na]+	159.512	30932474
AllCCS	[M+H]+	150.7	32859911
AllCCS	[M+H-H2O]+	146.9	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	151.9	32859911
AllCCS	[M+HCOO]-	152.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ecgonine Ethyl Ester	CCOC(=O)C1C2CCC(CC1O)N2C	2487.7	Standard polar	33892256
Ecgonine Ethyl Ester	CCOC(=O)C1C2CCC(CC1O)N2C	1580.0	Standard non polar	33892256
Ecgonine Ethyl Ester	CCOC(=O)C1C2CCC(CC1O)N2C	1627.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl ecgonine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003v-9500000000-96945efcc4ad0f4a0130	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl ecgonine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl ecgonine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl ecgonine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Ethyl ecgonine 10V, Positive-QTOF	splash10-01ot-0950000000-abd160e71041d15fd001	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 20V, Positive-QTOF	splash10-0hft-1910000000-8b9d63c1a61104e1f198	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 40V, Positive-QTOF	splash10-0uka-3900000000-f706ff8078f8068a51da	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 10V, Negative-QTOF	splash10-03di-0980000000-aaefaad7e26d8893f599	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 20V, Negative-QTOF	splash10-02fx-0920000000-8180fc8082ebb52b6501	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 40V, Negative-QTOF	splash10-006x-1900000000-ef94609073f2c3670589	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 10V, Positive-QTOF	splash10-03di-0090000000-2ee018097b945d126aad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 20V, Positive-QTOF	splash10-03xr-0950000000-3cbe1cb2526fcd2488c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 40V, Positive-QTOF	splash10-014j-9800000000-d9753459b34356aaa030	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 10V, Negative-QTOF	splash10-03di-0190000000-3e1d7428cd1c589f321a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 20V, Negative-QTOF	splash10-02t9-0940000000-2d2e36bc0d5f49bd73d1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl ecgonine 40V, Negative-QTOF	splash10-00di-0900000000-0e76a17a63d34c8a78e5	2021-10-12	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14808811

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 Ethyl ecgonine (HMDB0251685)

MOL for HMDB0251685 (Ethyl ecgonine)

3D MOL for HMDB0251685 (Ethyl ecgonine)

3D SDF for HMDB0251685 (Ethyl ecgonine)

3D-SDF for HMDB0251685 (Ethyl ecgonine)

PDB for HMDB0251685 (Ethyl ecgonine)

3D PDB for HMDB0251685 (Ethyl ecgonine)

SMILES for HMDB0251685 (Ethyl ecgonine)

INCHI for HMDB0251685 (Ethyl ecgonine)

Structure for HMDB0251685 (Ethyl ecgonine)

3D Structure for HMDB0251685 (Ethyl ecgonine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra