Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 05:46:51 UTC

Update Date

2021-09-14 15:45:58 UTC

HMDB ID

HMDB0006406

Secondary Accession Numbers

HMDB06406

Metabolite Identification

Common Name

Ecgonine methyl ester

Description

Ecgonine methyl ester, also known as methyl ecgonine, 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. Ecgonine methyl ester exists in all living organisms, ranging from bacteria to humans. Ecgonine methyl ester has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make ecgonine methyl ester a potential biomarker for the consumption of these foods. Ecgonine methyl ester is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Ecgonine methyl ester.

Structure

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

HMDB0006406
     RDKit          3D
Ecgonine methyl ester
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3208    0.6051    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    0.4868   -0.1399 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.4947    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271   -1.3059    1.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -0.5563   -0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0413    0.7056   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    1.1870   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.5391   -1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -0.3630   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -1.6945   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.7741    0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0542   -1.9143    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    0.3946    0.8632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    1.6206    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0049    0.2313   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.6522    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943   -0.0369    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460   -0.6346   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    1.4935    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459    0.8077   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    2.2729   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    1.3057   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012   -0.0527   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.5156    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -1.7586   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308   -2.5425   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -2.6832   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345   -2.8053    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753    1.4099    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    2.0121    2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393    2.4083    0.4161 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
  9 13  1  0
 13 14  1  0
 11  5  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv0541 02231220392D          

 14 15  0  0  1  0            999 V2000
   13.2472  -11.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6712  -12.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2737  -12.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5874   -8.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9815   -9.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1950   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7152  -10.9804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4926  -10.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7060   -9.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0478   -9.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9617  -10.6450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1748   -7.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8867  -11.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8426  -12.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  1  0  0  0
  2 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006406

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1

> <INCHI_KEY>
QIQNNBXHAYSQRY-ABIFROTESA-N

> <FORMULA>
C10H17NO3

> <MOLECULAR_WEIGHT>
199.2469

> <EXACT_MASS>
199.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.816593722450087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
-0.2131918396666671

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.5954100931088

> <JCHEM_PKA_STRONGEST_BASIC>
9.0392885149116

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
51.3384

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.87e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ecgonine methyl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006406
     RDKit          3D
Ecgonine methyl ester
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3208    0.6051    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    0.4868   -0.1399 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.4947    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271   -1.3059    1.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -0.5563   -0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0413    0.7056   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    1.1870   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.5391   -1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -0.3630   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -1.6945   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.7741    0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0542   -1.9143    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    0.3946    0.8632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    1.6206    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0049    0.2313   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.6522    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943   -0.0369    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460   -0.6346   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    1.4935    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459    0.8077   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    2.2729   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    1.3057   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012   -0.0527   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.5156    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -1.7586   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308   -2.5425   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -2.6832   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345   -2.8053    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753    1.4099    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    2.0121    2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393    2.4083    0.4161 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
  9 13  1  0
 13 14  1  0
 11  5  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      24.728 -20.641   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      29.253 -22.479   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.644 -23.033   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      29.097 -15.583   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      29.832 -18.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.231 -17.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.468 -20.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.653 -19.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.051 -18.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.223 -18.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.062 -19.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.326 -14.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.788 -22.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.573 -23.985   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   13   14                                                       
CONECT    3   13                                                            
CONECT    4    5    6   12                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5   11   13                                                  
CONECT    8    5    9                                                       
CONECT    9    6    8                                                       
CONECT   10    6   11                                                       
CONECT   11    1    7   10                                                  
CONECT   12    4                                                            
CONECT   13    2    3    7                                                  
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0006406
HETATM    1  C1  UNL     1       4.321   0.605   0.358  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.994   0.487  -0.140  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.119  -0.495   0.286  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.527  -1.306   1.147  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.738  -0.556  -0.283  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.041   0.706  -0.023  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.742   1.187  -1.277  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.101   0.539  -1.234  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.048  -0.363  -0.026  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.410  -1.695  -0.376  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.001  -1.774   0.168  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.054  -1.914   1.539  1.00  0.00           O  
HETATM   13  N1  UNL     1      -1.168   0.395   0.863  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.870   1.621   1.186  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.005   0.231  -0.461  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.619   1.652   0.530  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.494  -0.037   1.234  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.846  -0.635  -1.401  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.564   1.494   0.460  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.146   0.808  -2.159  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.762   2.273  -1.369  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.901   1.306  -1.097  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.301  -0.053  -2.148  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.045  -0.516   0.431  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.344  -1.759  -1.481  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.031  -2.542  -0.021  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.469  -2.683  -0.269  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.435  -2.805   1.736  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.975   1.410   1.223  1.00  0.00           H  
HETATM   30  H16 UNL     1      -1.583   2.012   2.187  1.00  0.00           H  
HETATM   31  H17 UNL     1      -1.739   2.408   0.416  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   11   18
CONECT    6    7   13   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   13   24
CONECT   10   11   25   26
CONECT   11   12   27
CONECT   12   28
CONECT   13   14
CONECT   14   29   30   31
END

HMDB0006406
     RDKit          3D
Ecgonine methyl ester
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3208    0.6051    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    0.4868   -0.1399 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.4947    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271   -1.3059    1.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -0.5563   -0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0413    0.7056   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    1.1870   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.5391   -1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -0.3630   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -1.6945   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.7741    0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0542   -1.9143    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    0.3946    0.8632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    1.6206    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0049    0.2313   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.6522    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943   -0.0369    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460   -0.6346   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    1.4935    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459    0.8077   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    2.2729   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    1.3057   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012   -0.0527   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.5156    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -1.7586   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308   -2.5425   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -2.6832   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345   -2.8053    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753    1.4099    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    2.0121    2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393    2.4083    0.4161 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
  9 13  1  0
 13 14  1  0
 11  5  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl ecgonine	Kegg

Chemical Formula

C₁₀H₁₇NO₃

Average Molecular Weight

199.2469

Monoisotopic Molecular Weight

199.120843415

IUPAC Name

methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

ecgonine methyl ester

CAS Registry Number

7143-09-1

SMILES

COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C

InChI Identifier

InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1

InChI Key

QIQNNBXHAYSQRY-ABIFROTESA-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
Methyl ester
Pyrrolidine
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Tropane alkaloids (C12448 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17132243)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006406)

Source

Endogenous

Endogenous (HMDB: HMDB0006406)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	587 g/L	ALOGPS
logP	0.14	ALOGPS
logP	-0.21	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	9.04	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	2	ChemAxon
Refractivity	51.34 m³·mol⁻¹	ChemAxon
Polarizability	20.82 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
DarkChem	[M+H]+	146.114	31661259
DarkChem	[M-H]-	143.642	31661259
DeepCCS	[M+H]+	147.797	30932474
DeepCCS	[M-H]-	145.439	30932474
DeepCCS	[M-2H]-	178.997	30932474
DeepCCS	[M+Na]+	154.085	30932474
AllCCS	[M+H]+	146.6	32859911
AllCCS	[M+H-H2O]+	142.6	32859911
AllCCS	[M+NH4]+	150.2	32859911
AllCCS	[M+Na]+	151.3	32859911
AllCCS	[M-H]-	146.3	32859911
AllCCS	[M+Na-2H]-	146.9	32859911
AllCCS	[M+HCOO]-	147.6	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.	2.69 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1407 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	289.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	575.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	86.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	43.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	258.3 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	264.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	723.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	616.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	66.6 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	718.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	707.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	468.5 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	309.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ecgonine methyl ester	COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C	2523.2	Standard polar	33892256
Ecgonine methyl ester	COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C	1495.3	Standard non polar	33892256
Ecgonine methyl ester	COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C	1564.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ecgonine methyl ester,1TMS,isomer #1	COC(=O)[C@@H]1C2CCC(C[C@@H]1O[Si](C)(C)C)N2C	1578.4	Semi standard non polar	33892256
Ecgonine methyl ester,1TBDMS,isomer #1	COC(=O)[C@@H]1C2CCC(C[C@@H]1O[Si](C)(C)C(C)(C)C)N2C	1787.2	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 - Ecgonine methyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9500000000-cf2ddf077b00040815cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine methyl ester GC-MS (1 TMS) - 70eV, Positive	splash10-007k-9320000000-2c7c73b58d1886e618c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine methyl ester 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOF	splash10-0udi-0090000000-6bb519514639540eac7e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOF	splash10-0f89-0950000000-117ad116d5ac14a5be9c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-507c3f3bafb08a0393f6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-daa82fab29c3bc26425a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOF	splash10-0g5i-0900000000-56c0d97c8ede7a0f5121	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOF	splash10-001i-0900000000-daa82fab29c3bc26425a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 30V, Positive-QTOF	splash10-001i-0900000000-fffbd1cb1619e5f92d43	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOF	splash10-0g5i-0900000000-56c0d97c8ede7a0f5121	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOF	splash10-0v5i-0900000000-a539dd19738540ffeecd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOF	splash10-0v5i-0900000000-de76b46915632e6c01da	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 30V, Positive-QTOF	splash10-001i-0900000000-687b3144e289411d4082	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOF	splash10-001i-0900000000-22aa62b28391bb713265	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOF	splash10-0f89-0950000000-ffcfa77b222d15829aaa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOF	splash10-0udi-0090000000-e3fcef6498db4fb940cc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOF	splash10-0ue9-0950000000-efcb591e326d6b910be4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOF	splash10-0ue9-1920000000-3866ea5e436094dba234	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOF	splash10-0fk9-3900000000-482ddc1485526a169412	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Negative-QTOF	splash10-0002-0900000000-2bd0a82ed0375eb83de6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Negative-QTOF	splash10-00rw-0900000000-3bc21f157c0540443956	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Negative-QTOF	splash10-00dl-1900000000-d566bd6e77d93dbf8b71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Negative-QTOF	splash10-0002-0900000000-10dc01597bf9d10d45eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Negative-QTOF	splash10-014j-0900000000-0e30c6026623a71a7a3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Negative-QTOF	splash10-00dl-6900000000-94cf39d3cb9ec7c8a4be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOF	splash10-0udi-0090000000-90ea4410b322d690d160	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOF	splash10-0udi-2790000000-9c3dd1d85b04ba825e6a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum

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 and Quantified	0.237 +/- 0.0150 uM	Adult (>18 years old)	Both	Normal	17132243	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

2267774

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443844

PDB ID

Not Available

ChEBI ID

708640

Food Biomarker Ontology

Not Available

VMH ID

EGME

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kline, Richard Harry, Jr. The synthesis and pharmacological activity of 3-arylecgonine methyl ester and 3-carbamoyloxyecgonine methyl ester analogs: probes for the characterization of the dopaminergic cocaine receptor. (1991), 127 pp. CAN 116:21292 AN 1992:21292

Material Safety Data Sheet (MSDS)

Not Available

General References

Roy IM, Jefferies TM, Threadgill MD, Dewar GH: Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):943-8. [PubMed:1298401 ]

Enzymes

Enzyme Details

1. Lysosomal acid lipase/cholesteryl ester hydrolase

General function:: Involved in lipid metabolic process
Specific function:: Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:: LIPA
Uniprot ID:: P38571
Molecular weight:: 45418.71

Enzyme Details

2. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Cocaine + Water → Ecgonine methyl ester + Benzoic acid	details

Enzyme Details

3. Cocaine esterase

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:: CES2
Uniprot ID:: O00748
Molecular weight:: 68898.39

Reactions

Cocaine + Water → Ecgonine methyl ester + Benzoic acid	details

Enzyme Details

4. Carboxylesterase 5A

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:: CES5A
Uniprot ID:: Q6NT32
Molecular weight:: 63925.82

Showing metabocard for Ecgonine methyl ester (HMDB0006406)

MOL for HMDB0006406 (Ecgonine methyl ester)

3D MOL for HMDB0006406 (Ecgonine methyl ester)

3D SDF for HMDB0006406 (Ecgonine methyl ester)

3D-SDF for HMDB0006406 (Ecgonine methyl ester)

PDB for HMDB0006406 (Ecgonine methyl ester)

3D PDB for HMDB0006406 (Ecgonine methyl ester)

SMILES for HMDB0006406 (Ecgonine methyl ester)

INCHI for HMDB0006406 (Ecgonine methyl ester)

Structure for HMDB0006406 (Ecgonine methyl ester)

3D Structure for HMDB0006406 (Ecgonine methyl ester)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions