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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 06:02:04 UTC

Update Date

2022-03-07 03:17:59 UTC

HMDB ID

HMDB0062751

Secondary Accession Numbers

HMDB62751

Metabolite Identification

Common Name

Ecgoninium Methyl Ester(1+)

Description

ecgoninium methyl ester(1+) belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom. The conjugate acid of ecgoninium methyl ester(1+) arising from protonation of the tertiary amino group; major species at pH 7.3. ecgoninium methyl ester(1+) is a very strong basic compound (based on its pKa).

Structure

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

HMDB0062751
     RDKit          3D
Ecgoninium Methyl Ester(1+)
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1425   -0.8157   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.5577    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    0.4726   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230    1.2207   -1.0518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.6034    0.3416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0599    1.7491   -0.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3723    1.9656   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    1.6883   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    0.2797    0.1055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7333    0.0124    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669   -1.0851    1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0071   -0.7254    0.1667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1696   -0.6032   -0.6805 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8227   -1.8249   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -1.9184    0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8401   -0.3154    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686   -0.5081   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7765    0.8554    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    2.6986    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    2.9373   -1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    1.8550   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    2.4371    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    0.1319   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2727    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    0.9022    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -2.0825    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -0.9657    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.5245   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -0.1568   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293   -1.6703   -0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -2.6973   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -2.0857   -2.0695 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
  6  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
 12  5  1  0
 13  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  1
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  13   1
M  END


  Mrv1652303231707022D          

 18 19  0  0  1  0            999 V2000
    1.0921    1.6407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757    0.8364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6307    0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757   -1.0173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0921   -1.8217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440   -0.0905    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2190   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -0.8338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8998   -0.7414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -1.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4102   -1.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930   -2.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074   -2.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -0.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8769    0.6081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -0.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
HMDB0062751

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@]([H])([NH+]1C)[C@@]([H])(C(=O)OC)[C@@]([H])(O)C2

> <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/p+1/t6-,7+,8-,9+/m0/s1

> <INCHI_KEY>
QIQNNBXHAYSQRY-UYXSQOIJSA-O

> <FORMULA>
C10H18NO3

> <MOLECULAR_WEIGHT>
200.257

> <EXACT_MASS>
200.128119864

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.39055416910719

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3S,5S)-3-hydroxy-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

> <ALOGPS_LOGP>
-1.58

> <JCHEM_LOGP>
-0.2131918396666671

> <ALOGPS_LOGS>
-2.04

> <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>
50.97

> <JCHEM_REFRACTIVITY>
62.35530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ecgoninium methyl ester(1+)

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062751
     RDKit          3D
Ecgoninium Methyl Ester(1+)
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1425   -0.8157   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.5577    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    0.4726   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230    1.2207   -1.0518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.6034    0.3416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0599    1.7491   -0.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3723    1.9656   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    1.6883   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    0.2797    0.1055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7333    0.0124    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669   -1.0851    1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0071   -0.7254    0.1667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1696   -0.6032   -0.6805 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8227   -1.8249   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -1.9184    0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8401   -0.3154    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686   -0.5081   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7765    0.8554    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    2.6986    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    2.9373   -1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    1.8550   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    2.4371    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    0.1319   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2727    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    0.9022    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -2.0825    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -0.9657    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.5245   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -0.1568   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293   -1.6703   -0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -2.6973   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -2.0857   -2.0695 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
  6  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
 12  5  1  0
 13  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  1
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  13   1
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0       2.039   3.063   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.381   1.561   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.177   0.601   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.177  -0.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.381  -1.899   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       2.039  -3.400   0.000  0.00  0.00           H+0
HETATM    7  N   UNK     0       1.949  -0.169   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0       0.409  -0.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.883  -1.556   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       5.413  -1.384   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       4.843  -2.760   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.366  -2.531   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.280  -4.194   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.240  -5.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.551  -0.169   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.370   1.135   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0       6.091  -0.169   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.883   1.219   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    9                                             
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    9   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0062751
HETATM    1  C1  UNL     1       4.142  -0.816  -0.086  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.816  -0.558   0.313  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.040   0.473  -0.196  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.523   1.221  -1.052  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.645   0.603   0.342  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.060   1.749  -0.298  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.372   1.966  -1.626  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.542   1.688  -0.274  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.014   0.280   0.106  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.733   0.012   1.546  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.667  -1.085   1.505  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.007  -0.725   0.167  1.00  0.00           C  
HETATM   13  N1  UNL     1      -1.170  -0.603  -0.681  1.00  0.00           N1+
HETATM   14  C10 UNL     1      -1.823  -1.825  -0.975  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.309  -1.918   0.070  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.840  -0.315   0.636  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.369  -0.508  -1.108  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.777   0.855   1.427  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.237   2.699   0.239  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.212   2.937  -1.850  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.973   1.855  -1.305  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.026   2.437   0.368  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.069   0.132  -0.138  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.593  -0.273   2.150  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.211   0.902   1.996  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.101  -2.082   1.492  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.078  -0.966   2.296  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.648  -1.524  -0.192  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.857  -0.157  -1.580  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.929  -1.670  -0.810  1.00  0.00           H  
HETATM   31  H17 UNL     1      -1.493  -2.697  -0.413  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.740  -2.086  -2.070  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   12   18
CONECT    6    7    8   19
CONECT    7   20
CONECT    8    9   21   22
CONECT    9   10   13   23
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   13   28
CONECT   13   14   29
CONECT   14   30   31   32
END

HMDB0062751
     RDKit          3D
Ecgoninium Methyl Ester(1+)
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1425   -0.8157   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.5577    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    0.4726   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230    1.2207   -1.0518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.6034    0.3416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0599    1.7491   -0.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3723    1.9656   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    1.6883   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    0.2797    0.1055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7333    0.0124    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669   -1.0851    1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0071   -0.7254    0.1667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1696   -0.6032   -0.6805 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8227   -1.8249   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -1.9184    0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8401   -0.3154    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686   -0.5081   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7765    0.8554    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    2.6986    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    2.9373   -1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    1.8550   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    2.4371    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    0.1319   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2727    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    0.9022    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -2.0825    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -0.9657    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.5245   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -0.1568   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293   -1.6703   -0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -2.6973   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -2.0857   -2.0695 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
  6  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
 12  5  1  0
 13  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  1
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  CHG  1  13   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ecgonine methyl ester	ChEBI
Ecgonine methyl ester hydrochloride, (1R-(exo,exo))-isomer	HMDB
Ecgonine methyl ester, (1R-(2-endo,3-exo))-isomer	HMDB
Ecgonine methyl ester, (1R-(2-exo,3-endo))-isomer	HMDB
Ecgonine methyl ester, (1R-(endo,endo))-isomer	HMDB
Ecgonine methyl ester, (1S-(endo,endo))-isomer	HMDB
Methyl ecgonine	HMDB

Chemical Formula

C₁₀H₁₈NO₃

Average Molecular Weight

200.257

Monoisotopic Molecular Weight

200.128119864

IUPAC Name

(1R,2R,3S,5S)-3-hydroxy-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

Traditional Name

ecgoninium methyl ester(1+)

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@]([H])([NH+]1C)[C@@]([H])(C(=O)OC)[C@@]([H])(O)C2

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/p+1/t6-,7+,8-,9+/m0/s1

InChI Key

QIQNNBXHAYSQRY-UYXSQOIJSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta amino acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

ammonium ion (CHEBI:59908 )

Ontology

Not Available

Not Available

Not Available

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	2.17 g/l	ALOGPS
LogP	-1.58	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-0.21	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.36 m³·mol⁻¹	ChemAxon
Polarizability	21.39 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-2H]-	172.163	30932474
DeepCCS	[M+Na]+	146.169	30932474
AllCCS	[M+H]+	144.5	32859911
AllCCS	[M+H-H2O]+	140.7	32859911
AllCCS	[M+NH4]+	148.0	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	147.1	32859911
AllCCS	[M+Na-2H]-	147.5	32859911
AllCCS	[M+HCOO]-	148.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ecgoninium Methyl Ester(1+)	[H][C@@]12CC[C@@]([H])([NH+]1C)[C@@]([H])(C(=O)OC)[C@@]([H])(O)C2	2623.4	Standard polar	33892256
Ecgoninium Methyl Ester(1+)	[H][C@@]12CC[C@@]([H])([NH+]1C)[C@@]([H])(C(=O)OC)[C@@]([H])(O)C2	1493.8	Standard non polar	33892256
Ecgoninium Methyl Ester(1+)	[H][C@@]12CC[C@@]([H])([NH+]1C)[C@@]([H])(C(=O)OC)[C@@]([H])(O)C2	1570.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ecgoninium Methyl Ester(1+),1TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H]2CC[C@H]1[NH+]2C	1674.2	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),1TMS,isomer #2	COC(=O)[C@H]1[C@@H](O)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C	1717.6	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C	1727.0	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C	1791.0	Standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C	2294.1	Standard polar	33892256
Ecgoninium Methyl Ester(1+),1TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]1[NH+]2C	1843.2	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),1TBDMS,isomer #2	COC(=O)[C@H]1[C@@H](O)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C(C)(C)C	1940.3	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C(C)(C)C	2185.5	Semi standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C(C)(C)C	2276.8	Standard non polar	33892256
Ecgoninium Methyl Ester(1+),2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]1[N+]2(C)[Si](C)(C)C(C)(C)C	2524.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgoninium Methyl Ester(1+) GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9500000000-ba3bbabbb6a3d4563eef	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgoninium Methyl Ester(1+) GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9430000000-dde74e21c6d91fa00dbf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgoninium Methyl Ester(1+) 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 - Ecgoninium Methyl Ester(1+) 10V, Positive-QTOF	splash10-0f89-0920000000-9e374184183854c90c57	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgoninium Methyl Ester(1+) 20V, Positive-QTOF	splash10-0ff0-1900000000-86fe76afabe6dbff7a71	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgoninium Methyl Ester(1+) 40V, Positive-QTOF	splash10-00dm-8900000000-4382f430261e976a172f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgoninium Methyl Ester(1+) 10V, Positive-QTOF	splash10-0ue9-1690000000-ebf8f853e285d3a6daf2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgoninium Methyl Ester(1+) 20V, Positive-QTOF	splash10-001j-9520000000-85c391b6b9fbc0033e1e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgoninium Methyl Ester(1+) 40V, Positive-QTOF	splash10-000t-9800000000-a08b988edeb39a62ecc0	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

Not Available

PDB ID

Not Available

ChEBI ID

59908

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Ecgoninium Methyl Ester(1+) (HMDB0062751)

MOL for HMDB0062751 (Ecgoninium Methyl Ester(1+))

3D MOL for HMDB0062751 (Ecgoninium Methyl Ester(1+))

3D SDF for HMDB0062751 (Ecgoninium Methyl Ester(1+))

3D-SDF for HMDB0062751 (Ecgoninium Methyl Ester(1+))

PDB for HMDB0062751 (Ecgoninium Methyl Ester(1+))

3D PDB for HMDB0062751 (Ecgoninium Methyl Ester(1+))

SMILES for HMDB0062751 (Ecgoninium Methyl Ester(1+))

INCHI for HMDB0062751 (Ecgoninium Methyl Ester(1+))

Structure for HMDB0062751 (Ecgoninium Methyl Ester(1+))

3D Structure for HMDB0062751 (Ecgoninium Methyl Ester(1+))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra