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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:47:23 UTC

Update Date

2021-09-26 22:50:38 UTC

HMDB ID

HMDB0243539

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Isopilocarpine

Description

(+)-Isopilocarpine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Based on a literature review a small amount of articles have been published on (+)-Isopilocarpine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-isopilocarpine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Isopilocarpine 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

HMDB0243539
     RDKit          3D
(+)-Isopilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.1904    0.9184    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    0.6474    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -0.6982   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -0.5258   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.8789   -1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.1480   -2.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2228   -0.0119   -1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -1.1073   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -1.4555   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5036   -0.5080    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -0.3256    2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    0.6490    2.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.0728    1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582    0.3811    0.4676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    0.6112   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -0.0131    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    1.5224    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.4944   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.8018    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615    1.4591   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079   -1.4548    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901    0.8599   -1.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -0.4046   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.0057   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8557   -0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571   -2.3817    0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953   -0.9030    2.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813    1.8769    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154   -0.1865   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    1.5994   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.6745   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  8  3  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
  3 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv0541 04121517052D          

 15 16  0  0  0  0            999 V2000
    1.8185    0.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004   -1.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981   -1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -1.9802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -2.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119   -2.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974   -2.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -1.9248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655   -1.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809   -0.8852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243539

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1C(CC2=CN=CN2C)COC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3

> <INCHI_KEY>
QCHFTSOMWOSFHM-UHFFFAOYSA-N

> <FORMULA>
C11H16N2O2

> <MOLECULAR_WEIGHT>
208.261

> <EXACT_MASS>
208.121177763

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.793214307252526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.949751419333334

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.608666134549649

> <JCHEM_POLAR_SURFACE_AREA>
44.120000000000005

> <JCHEM_REFRACTIVITY>
56.534200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xi,xi-pilocarpine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243539
     RDKit          3D
(+)-Isopilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.1904    0.9184    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    0.6474    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -0.6982   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -0.5258   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.8789   -1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.1480   -2.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2228   -0.0119   -1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -1.1073   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -1.4555   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5036   -0.5080    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -0.3256    2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    0.6490    2.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.0728    1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582    0.3811    0.4676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    0.6112   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -0.0131    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    1.5224    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.4944   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.8018    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615    1.4591   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079   -1.4548    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901    0.8599   -1.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -0.4046   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.0057   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8557   -0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571   -2.3817    0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953   -0.9030    2.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813    1.8769    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154   -0.1865   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    1.5994   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.6745   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  8  3  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
  3 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       3.395   1.087   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.728   0.317   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.728  -1.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.974  -2.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.439  -1.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.583  -2.683   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.090  -2.363   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.860  -3.696   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.829  -4.841   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       8.422  -4.214   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.089  -4.984   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.498  -3.593   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.958  -3.593   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.482  -2.128   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.018  -1.652   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0243539
HETATM    1  C1  UNL     1       3.190   0.918   0.786  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.694   0.647   0.535  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.617  -0.698  -0.090  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.438  -0.526  -1.356  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.593  -0.879  -1.621  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.590   0.148  -2.214  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.223  -0.012  -1.810  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.367  -1.107  -0.744  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.836  -1.455  -0.035  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.504  -0.508   0.843  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.310  -0.326   2.196  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.129   0.649   2.620  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.824   1.073   1.559  1.00  0.00           C  
HETATM   14  N2  UNL     1      -2.458   0.381   0.468  1.00  0.00           N  
HETATM   15  C11 UNL     1      -3.036   0.611  -0.837  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.753  -0.013   0.898  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.339   1.522   1.697  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.625   1.494  -0.051  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.213   0.802   1.487  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.361   1.459  -0.148  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.108  -1.455   0.528  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.190   0.860  -1.311  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.396  -0.405  -2.649  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.653  -2.006  -1.394  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.581  -1.856  -0.794  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.657  -2.382   0.596  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.595  -0.903   2.786  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.581   1.877   1.609  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.815  -0.187  -1.559  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.691   1.599  -1.209  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.160   0.674  -0.785  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    8   21
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   22   23
CONECT    8    9   24
CONECT    9   10   25   26
CONECT   10   11   11   14
CONECT   11   12   27
CONECT   12   13   13
CONECT   13   14   28
CONECT   14   15
CONECT   15   29   30   31
END

HMDB0243539
     RDKit          3D
(+)-Isopilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.1904    0.9184    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    0.6474    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -0.6982   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -0.5258   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.8789   -1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.1480   -2.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2228   -0.0119   -1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -1.1073   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -1.4555   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5036   -0.5080    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -0.3256    2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    0.6490    2.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.0728    1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582    0.3811    0.4676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    0.6112   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -0.0131    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    1.5224    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.4944   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.8018    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615    1.4591   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1079   -1.4548    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901    0.8599   -1.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -0.4046   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.0057   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8557   -0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571   -2.3817    0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953   -0.9030    2.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813    1.8769    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154   -0.1865   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    1.5994   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.6745   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  8  3  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
  3 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆N₂O₂

Average Molecular Weight

208.261

Monoisotopic Molecular Weight

208.121177763

IUPAC Name

3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one

Traditional Name

xi,xi-pilocarpine

CAS Registry Number

Not Available

SMILES

CCC1C(CC2=CN=CN2C)COC1=O

InChI Identifier

InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3

InChI Key

QCHFTSOMWOSFHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Gamma butyrolactone
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:39460 )
butan-4-olide (CHEBI:39460 )

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	1.15	ALOGPS
logP	0.95	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	6.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.53 m³·mol⁻¹	ChemAxon
Polarizability	21.79 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]+	146.555	30932474
DeepCCS	[M-H]-	142.728	30932474
DeepCCS	[M-2H]-	180.233	30932474
DeepCCS	[M+Na]+	155.839	30932474
AllCCS	[M+H]+	146.5	32859911
AllCCS	[M+H-H2O]+	142.4	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	149.9	32859911
AllCCS	[M+Na-2H]-	150.3	32859911
AllCCS	[M+HCOO]-	150.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Isopilocarpine	CCC1C(CC2=CN=CN2C)COC1=O	2689.2	Standard polar	33892256
(+)-Isopilocarpine	CCC1C(CC2=CN=CN2C)COC1=O	1963.5	Standard non polar	33892256
(+)-Isopilocarpine	CCC1C(CC2=CN=CN2C)COC1=O	1989.1	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 - (+)-Isopilocarpine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-dadfea39cdf9ef51bb38	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Isopilocarpine 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 - (+)-Isopilocarpine 6V, Positive-QTOF	splash10-0a4i-1090000000-2fd25e6044f26134a0aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Isopilocarpine 6V, Positive-QTOF	splash10-0a4i-1090000000-a96142a7f969311e7a5b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 10V, Positive-QTOF	splash10-0a4i-1390000000-5ff1bbd1b734b6351ce5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 20V, Positive-QTOF	splash10-0a4j-9740000000-f3742430bedb805a2901	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 40V, Positive-QTOF	splash10-0592-9200000000-d339d7cbece04bdd1f88	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 10V, Negative-QTOF	splash10-0a4i-1190000000-fe6991830124468537e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 20V, Negative-QTOF	splash10-052b-9440000000-70e476186bca183b4e48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Isopilocarpine 40V, Negative-QTOF	splash10-05o0-9200000000-42d2f984d5575550c9ad	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

4653

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4819

PDB ID

Not Available

ChEBI ID

39460

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 (+)-Isopilocarpine (HMDB0243539)

MOL for HMDB0243539 ((+)-Isopilocarpine)

3D MOL for HMDB0243539 ((+)-Isopilocarpine)

3D SDF for HMDB0243539 ((+)-Isopilocarpine)

3D-SDF for HMDB0243539 ((+)-Isopilocarpine)

PDB for HMDB0243539 ((+)-Isopilocarpine)

3D PDB for HMDB0243539 ((+)-Isopilocarpine)

SMILES for HMDB0243539 ((+)-Isopilocarpine)

INCHI for HMDB0243539 ((+)-Isopilocarpine)

Structure for HMDB0243539 ((+)-Isopilocarpine)

3D Structure for HMDB0243539 ((+)-Isopilocarpine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra