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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:27 UTC

HMDB ID

HMDB0015217

Secondary Accession Numbers

HMDB15217

Metabolite Identification

Common Name

Pilocarpine

Description

Pilocarpine, also known as ocusert pilo-20 or adsorbocarpine, 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. Pilocarpine is a drug which is used for the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with sjögrens syndrome. Pilocarpine 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 a significant number of articles have been published on Pilocarpine.

Structure

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

HMDB0015217
     RDKit          3D
Pilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7228   -1.0620    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.1722    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661    0.2124    0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1533    1.0991   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.9471   -0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    2.1298   -0.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567    1.8176    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    0.2805    0.5284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2167   -0.2750   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.3080   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -0.6275   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3258   -0.6154   -2.5473 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834   -0.3061   -1.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -0.1117   -0.4509 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    0.2096    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -1.2847   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.7501    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327   -0.0463    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0151   -1.7566   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -1.6917    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.6708    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1353   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    2.2233    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.1069    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236   -1.3066   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927    0.3877   -1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -0.8480   -3.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8134   -0.2144   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726   -0.6413    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    1.1875    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2465    1.1684 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  1
  7 22  1  0
  7 23  1  0
  8 24  1  1
  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

1085
  Mrv0541 02231215142D          

 15 16  0  0  1  0            999 V2000
    4.1277   -1.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8178   -2.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834    0.7557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3229    2.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.1463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0478   -0.6312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7152    0.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -1.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4297    1.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7354    1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3549   -0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 13  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  5  8  1  0  0  0  0
  6  9  1  1  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015217

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H]1[C@@H](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/t8-,10-/m0/s1

> <INCHI_KEY>
QCHFTSOMWOSFHM-WPRPVWTQSA-N

> <FORMULA>
C11H16N2O2

> <MOLECULAR_WEIGHT>
208.2569

> <EXACT_MASS>
208.121177766

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.339274631387376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-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>
6.608666134549648

> <JCHEM_POLAR_SURFACE_AREA>
44.120000000000005

> <JCHEM_REFRACTIVITY>
56.53419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pilocarpine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015217
     RDKit          3D
Pilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7228   -1.0620    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.1722    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661    0.2124    0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1533    1.0991   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.9471   -0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    2.1298   -0.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567    1.8176    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    0.2805    0.5284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2167   -0.2750   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.3080   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -0.6275   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3258   -0.6154   -2.5473 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834   -0.3061   -1.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -0.1117   -0.4509 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    0.2096    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -1.2847   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.7501    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327   -0.0463    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0151   -1.7566   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -1.6917    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.6708    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1353   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    2.2233    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.1069    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236   -1.3066   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927    0.3877   -1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -0.8480   -3.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8134   -0.2144   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726   -0.6413    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    1.1875    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2465    1.1684 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  1
  7 22  1  0
  7 23  1  0
  8 24  1  1
  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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1085                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.705  -2.643   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.260  -3.889   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.676   1.411   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.936   3.889   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.935  -0.273   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.689  -1.178   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.935   1.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.181  -1.178   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.224  -0.702   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.165  -2.643   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.269   2.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -1.733   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.430   3.569   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.706   2.555   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.996  -0.096   0.000  0.00  0.00           C+0
CONECT    1    8   10                                                       
CONECT    2   10                                                            
CONECT    3   11   14   15                                                  
CONECT    4   13   14                                                       
CONECT    5    6    7    8                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5   11                                                       
CONECT    8    1    5                                                       
CONECT    9    6   12                                                       
CONECT   10    1    2    6                                                  
CONECT   11    3    7   13                                                  
CONECT   12    9                                                            
CONECT   13    4   11                                                       
CONECT   14    3    4                                                       
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0015217
HETATM    1  C1  UNL     1      -3.723  -1.062   0.917  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.200  -1.172   0.762  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.666   0.212   0.771  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.153   1.099  -0.285  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.202   0.947  -0.958  1.00  0.00           O  
HETATM    6  O2  UNL     1      -1.211   2.130  -0.375  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.057   1.818   0.398  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.144   0.281   0.528  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.217  -0.275  -0.788  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.640  -0.308  -1.155  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.999  -0.628  -2.481  1.00  0.00           C  
HETATM   12  N1  UNL     1       3.326  -0.615  -2.547  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.783  -0.306  -1.331  1.00  0.00           C  
HETATM   14  N2  UNL     1       2.758  -0.112  -0.451  1.00  0.00           N  
HETATM   15  C11 UNL     1       2.897   0.210   0.963  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.233  -1.285  -0.051  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.099  -1.750   1.700  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.033  -0.046   1.202  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.015  -1.757  -0.137  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.846  -1.692   1.682  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.812   0.671   1.766  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.855   2.135  -0.118  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.176   2.223   1.417  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.318  -0.107   1.417  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.224  -1.307  -0.962  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.293   0.388  -1.561  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.353  -0.848  -3.319  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.813  -0.214  -1.050  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.573  -0.641   1.621  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.541   1.187   1.258  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.015   0.246   1.168  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

HMDB0015217
     RDKit          3D
Pilocarpine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7228   -1.0620    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.1722    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661    0.2124    0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1533    1.0991   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.9471   -0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2113    2.1298   -0.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567    1.8176    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    0.2805    0.5284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2167   -0.2750   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.3080   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -0.6275   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3258   -0.6154   -2.5473 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834   -0.3061   -1.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -0.1117   -0.4509 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    0.2096    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -1.2847   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.7501    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327   -0.0463    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0151   -1.7566   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -1.6917    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.6708    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1353   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    2.2233    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.1069    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236   -1.3066   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927    0.3877   -1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -0.8480   -3.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8134   -0.2144   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726   -0.6413    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    1.1875    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    0.2465    1.1684 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  1
  7 22  1  0
  7 23  1  0
  8 24  1  1
  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

Value	Source
(3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone	ChEBI
(3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone	ChEBI
Ocusert pilo-20	Kegg
Adsorbocarpine	HMDB
beta-Pilocarpine hydrochloride	HMDB
Pilocarpin	HMDB
Pilocarpine chloride	HMDB
Pilocarpine HCL	HMDB
Pilocarpine hydrochloride	HMDB
Pilocarpine monohydrochloride	HMDB
Pilocarpine muriate	HMDB
Pilokarpin	HMDB
Pilokarpin monohydrochloride	HMDB
Spersacarpine	HMDB
Spersacarpine hydrochloride	HMDB
Hydrochloride, pilocarpine	HMDB
Isopilocarpine	HMDB
Nitrate, pilocarpine	HMDB
Pilocarpine mononitrate, (3S-cis)-isomer	HMDB
Pilocarpine, monohydrochloride, (3S-cis)-isomer	HMDB
Salagen	HMDB
Ocusert	HMDB
Isoptocarpine	HMDB
Pilocarpine nitrate	HMDB
Pilocarpine	ChEBI

Chemical Formula

C₁₁H₁₆N₂O₂

Average Molecular Weight

208.2569

Monoisotopic Molecular Weight

208.121177766

IUPAC Name

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

Traditional Name

pilocarpine

CAS Registry Number

54-71-7

SMILES

CC[C@H]1[C@@H](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/t8-,10-/m0/s1

InChI Key

QCHFTSOMWOSFHM-WPRPVWTQSA-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

pilocarpine (CHEBI:8207 )
Imidazole alkaloids (C07474 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Sweat (PMID: 26755145)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	34 °C	Not Available
Boiling Point	431.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.07 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	146.357	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001360

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.07 g/L	ALOGPS
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	22.34 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]+	147.478	31661259
DarkChem	[M-H]-	147.008	31661259
DeepCCS	[M+H]+	146.704	30932474
DeepCCS	[M-H]-	144.308	30932474
DeepCCS	[M-2H]-	177.444	30932474
DeepCCS	[M+Na]+	152.636	30932474
AllCCS	[M+H]+	146.0	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	149.8	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	151.1	32859911
AllCCS	[M+HCOO]-	151.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pilocarpine	CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O	2686.0	Standard polar	33892256
Pilocarpine	CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O	1938.7	Standard non polar	33892256
Pilocarpine	CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O	1934.9	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 - Pilocarpine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-dadfea39cdf9ef51bb38	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pilocarpine 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 - Pilocarpine 6V, Positive-QTOF	splash10-0a4i-1090000000-2fd25e6044f26134a0aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 30V, Positive-QTOF	splash10-0002-9400000000-20a06057a274f78a95cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-0090000000-defeea6e1be7da5df19c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 40V, Positive-QTOF	splash10-0002-9000000000-cb6dd4c8fd9faf642a5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 50V, Positive-QTOF	splash10-0002-9100000000-a58d77d501ea8e44d237	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-1090000000-90bbfd0f103bf2df2350	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 20V, Positive-QTOF	splash10-0a4j-5290000000-d69679a4b81e0442184f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 6V, Positive-QTOF	splash10-0a4i-1190000000-b781ed76499fdad467c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-1090000000-a96142a7f969311e7a5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 35V, Positive-QTOF	splash10-0a4j-7790000000-914d8ed86ae8535d11fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 6V, Positive-QTOF	splash10-0002-9300000000-ad4d9d6aa3e5e27b8fc3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-0090000000-2df89b2b774b30adf514	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-0090000000-bb2a8fea255c0847828f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 30V, Positive-QTOF	splash10-0002-9300000000-3efb8b2920ff65a813d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 20V, Positive-QTOF	splash10-052b-9580000000-49f5b565991796fac6e9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-0090000000-6baeabdd0794d63b5d1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 50V, Positive-QTOF	splash10-0002-9100000000-2a0733ac2670b486cead	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-1190000000-7cb82eee0859eb856641	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pilocarpine 50V, Positive-QTOF	splash10-0002-9100000000-9d497ccde6e92e5082ac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 10V, Positive-QTOF	splash10-0a4i-0690000000-786fb6f080bd545dbc39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 20V, Positive-QTOF	splash10-0cka-1920000000-56d387d24bcc6e2e3637	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 40V, Positive-QTOF	splash10-0006-9300000000-e57c52a1b125f83b1903	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 10V, Negative-QTOF	splash10-0a4i-0190000000-fc43dc1afe8440f3e607	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 20V, Negative-QTOF	splash10-0bt9-1930000000-b7fcb5510042754cd666	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilocarpine 40V, Negative-QTOF	splash10-0a4j-9800000000-0f44a4b4787f9e119567	2016-08-03	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Sweat
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01085	21059682	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01085	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Sweat	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	screen-positive CF	Adriana Nori...	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]

Associated OMIM IDs

219700 (Cystic fibrosis)

External Links

DrugBank ID

DB01085

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002355

Chemspider ID

5699

KEGG Compound ID

C07474

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pilocarpine

METLIN ID

Not Available

PubChem Compound

5910

PDB ID

9PL

ChEBI ID

8207

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Sykes DA, Dowling MR, Charlton SJ: Exploring the mechanism of agonist efficacy: a relationship between efficacy and agonist dissociation rate at the muscarinic M3 receptor. Mol Pharmacol. 2009 Sep;76(3):543-51. doi: 10.1124/mol.108.054452. Epub 2009 Jun 4. [PubMed:19498041 ]
Figueroa KW, Griffin MT, Ehlert FJ: Selectivity of agonists for the active state of M1 to M4 muscarinic receptor subtypes. J Pharmacol Exp Ther. 2009 Jan;328(1):331-42. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613 ]

Enzyme Details

5. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Figueroa KW, Griffin MT, Ehlert FJ: Selectivity of agonists for the active state of M1 to M4 muscarinic receptor subtypes. J Pharmacol Exp Ther. 2009 Jan;328(1):331-42. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Moreno-Vinasco L, Verbout NG, Fryer AD, Jacoby DB: Retinoic acid prevents virus-induced airway hyperreactivity and M2 receptor dysfunction via anti-inflammatory and antiviral effects. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L340-6. doi: 10.1152/ajplung.90267.2008. Epub 2009 May 22. [PubMed:19465517 ]
Figueroa KW, Griffin MT, Ehlert FJ: Selectivity of agonists for the active state of M1 to M4 muscarinic receptor subtypes. J Pharmacol Exp Ther. 2009 Jan;328(1):331-42. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613 ]

Showing metabocard for Pilocarpine (HMDB0015217)

MOL for HMDB0015217 (Pilocarpine)

3D MOL for HMDB0015217 (Pilocarpine)

3D SDF for HMDB0015217 (Pilocarpine)

3D-SDF for HMDB0015217 (Pilocarpine)

PDB for HMDB0015217 (Pilocarpine)

3D PDB for HMDB0015217 (Pilocarpine)

SMILES for HMDB0015217 (Pilocarpine)

INCHI for HMDB0015217 (Pilocarpine)

Structure for HMDB0015217 (Pilocarpine)

3D Structure for HMDB0015217 (Pilocarpine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References

References

References

References

References