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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015292

Secondary Accession Numbers

HMDB15292

Metabolite Identification

Common Name

Chloroprocaine

Description

Chloroprocaine hydrochloride is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine, like other local anesthetics, blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse and by reducing the rate of rise of the action potential.

Structure

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

HMDB0015292
     RDKit          3D
Chloroprocaine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -3.9962   -2.0820   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1161   -1.3127    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -0.0828    0.8303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8122    0.8374   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.2283   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -0.4933    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6090    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.0501    0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    0.8657    0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3395    2.0956    0.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727    0.3908    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237   -0.6031    1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -1.0108    0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446   -0.4288   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7818   -0.8199   -0.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006    0.5726   -0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.9652   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8647    2.2424   -1.5724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.4751   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105   -2.8893   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9522   -2.6756   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332   -0.9254    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165   -1.8891    1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564    0.5079   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309    0.8964    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    2.5303   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    2.9608   -0.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    2.4544    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.2608    1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -1.0255   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    1.3756   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322    1.1006    1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -1.0763    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1899   -1.7976    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5407   -0.4821    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -1.4301   -1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    1.0770   -1.6864 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  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
M  END

1161
  Mrv0541 02231215172D          

 18 18  0  0  0  0            999 V2000
    1.6500   -0.9034    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.3967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  9  1  0  0  0  0
  2 12  1  0  0  0  0
  3 12  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015292

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3

> <INCHI_KEY>
VDANGULDQQJODZ-UHFFFAOYSA-N

> <FORMULA>
C13H19ClN2O2

> <MOLECULAR_WEIGHT>
270.755

> <EXACT_MASS>
270.113505569

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.73575721920887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(diethylamino)ethyl 4-amino-2-chlorobenzoate

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.4841019340000003

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.96155163061007

> <JCHEM_POLAR_SURFACE_AREA>
55.56

> <JCHEM_REFRACTIVITY>
75.10480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroprocaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015292
     RDKit          3D
Chloroprocaine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -3.9962   -2.0820   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1161   -1.3127    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -0.0828    0.8303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8122    0.8374   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.2283   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -0.4933    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6090    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.0501    0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    0.8657    0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3395    2.0956    0.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727    0.3908    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237   -0.6031    1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -1.0108    0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446   -0.4288   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7818   -0.8199   -0.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006    0.5726   -0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.9652   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8647    2.2424   -1.5724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.4751   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105   -2.8893   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9522   -2.6756   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332   -0.9254    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165   -1.8891    1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564    0.5079   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309    0.8964    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    2.5303   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    2.9608   -0.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    2.4544    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.2608    1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -1.0255   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    1.3756   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322    1.1006    1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -1.0763    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1899   -1.7976    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5407   -0.4821    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -1.4301   -1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    1.0770   -1.6864 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  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1161                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -1.686   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.081   0.624   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414   0.624   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.415   4.474   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.748  -6.306   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.415   2.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748   5.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   5.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   2.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   6.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   6.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -0.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -1.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -2.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -2.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -3.996   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    9   12                                                       
CONECT    3   12                                                            
CONECT    4    6    7    8                                                  
CONECT    5   16                                                            
CONECT    6    4    9                                                       
CONECT    7    4   10                                                       
CONECT    8    4   11                                                       
CONECT    9    2    6                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    2    3   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14    1   13   17                                                  
CONECT   15   13   18                                                       
CONECT   16    5   17   18                                                  
CONECT   17   14   16                                                       
CONECT   18   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0015292
HETATM    1  C1  UNL     1      -3.996  -2.082  -0.449  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.116  -1.313   0.813  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.264  -0.083   0.830  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.812   0.837  -0.130  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.274   2.228  -0.054  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.915  -0.493   0.626  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.924   0.609   0.755  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.413   0.050   0.539  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.512   0.866   0.609  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.340   2.096   0.869  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.873   0.391   0.395  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.424  -0.603   1.158  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.709  -1.011   0.910  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.445  -0.429  -0.098  1.00  0.00           C  
HETATM   15  N2  UNL     1       6.782  -0.820  -0.393  1.00  0.00           N  
HETATM   16  C12 UNL     1       4.901   0.573  -0.874  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.627   0.965  -0.616  1.00  0.00           C  
HETATM   18 CL1  UNL     1       2.865   2.242  -1.572  1.00  0.00          CL  
HETATM   19  H1  UNL     1      -3.901  -1.475  -1.346  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.211  -2.889  -0.385  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.952  -2.676  -0.574  1.00  0.00           H  
HETATM   22  H4  UNL     1      -5.133  -0.925   0.969  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.816  -1.889   1.688  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.656   0.508  -1.192  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.931   0.896   0.003  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.686   2.530  -0.968  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.160   2.961  -0.100  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.764   2.454   0.903  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.650  -1.261   1.393  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.775  -1.025  -0.355  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.972   1.376  -0.074  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.932   1.101   1.743  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.853  -1.076   1.955  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.190  -1.798   1.494  1.00  0.00           H  
HETATM   35  H17 UNL     1       7.541  -0.482   0.225  1.00  0.00           H  
HETATM   36  H18 UNL     1       6.938  -1.430  -1.220  1.00  0.00           H  
HETATM   37  H19 UNL     1       5.430   1.077  -1.686  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    6
CONECT    4    5   24   25
CONECT    5   26   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35   36
CONECT   16   17   17   37
CONECT   17   18
END

HMDB0015292
     RDKit          3D
Chloroprocaine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -3.9962   -2.0820   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1161   -1.3127    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -0.0828    0.8303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8122    0.8374   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.2283   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -0.4933    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6090    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.0501    0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    0.8657    0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3395    2.0956    0.8690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727    0.3908    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237   -0.6031    1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -1.0108    0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446   -0.4288   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7818   -0.8199   -0.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006    0.5726   -0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.9652   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8647    2.2424   -1.5724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.4751   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105   -2.8893   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9522   -2.6756   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332   -0.9254    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165   -1.8891    1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564    0.5079   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309    0.8964    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    2.5303   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    2.9608   -0.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    2.4544    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.2608    1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -1.0255   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    1.3756   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322    1.1006    1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -1.0763    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1899   -1.7976    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5407   -0.4821    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -1.4301   -1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    1.0770   -1.6864 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  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Chloroprocaine	ChEBI
4-Amino-2-chlorobenzoic acid 2-(diethylamino)ethyl ester	ChEBI
Chloroprocain	ChEBI
Chloroprocainum	ChEBI
Cloroprocaina	ChEBI
4-Amino-2-chlorobenzoate 2-(diethylamino)ethyl ester	Generator
Chlorprocaine	HMDB
Nesacaine MPF	HMDB
Chlor-procaine	HMDB
Nesacaine	HMDB
Chloroprocaine hydrochloride	HMDB

Chemical Formula

C₁₃H₁₉ClN₂O₂

Average Molecular Weight

270.755

Monoisotopic Molecular Weight

270.113505569

IUPAC Name

2-(diethylamino)ethyl 4-amino-2-chlorobenzoate

Traditional Name

chloroprocaine

CAS Registry Number

133-16-4

SMILES

CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1

InChI Identifier

InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3

InChI Key

VDANGULDQQJODZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
2-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Vinylogous halide
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:3636 )
benzoate ester (CHEBI:3636 )

Ontology

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	1.3 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.3 g/L	ALOGPS
logP	2.72	ALOGPS
logP	2.48	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	75.1 m³·mol⁻¹	ChemAxon
Polarizability	28.74 Å³	ChemAxon
Number of Rings	1	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]+	165.558	30932474
DeepCCS	[M-H]-	163.2	30932474
DeepCCS	[M-2H]-	196.085	30932474
DeepCCS	[M+Na]+	171.651	30932474
AllCCS	[M+H]+	160.8	32859911
AllCCS	[M+H-H2O]+	157.5	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	163.8	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	165.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chloroprocaine	CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1	3200.0	Standard polar	33892256
Chloroprocaine	CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1	2145.5	Standard non polar	33892256
Chloroprocaine	CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1	2223.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chloroprocaine,1TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1Cl	2332.9	Semi standard non polar	33892256
Chloroprocaine,1TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1Cl	2286.1	Standard non polar	33892256
Chloroprocaine,1TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1Cl	2700.0	Standard polar	33892256
Chloroprocaine,2TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2257.7	Semi standard non polar	33892256
Chloroprocaine,2TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2316.3	Standard non polar	33892256
Chloroprocaine,2TMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2546.2	Standard polar	33892256
Chloroprocaine,1TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1Cl	2515.8	Semi standard non polar	33892256
Chloroprocaine,1TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1Cl	2511.6	Standard non polar	33892256
Chloroprocaine,1TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1Cl	2776.7	Standard polar	33892256
Chloroprocaine,2TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2618.8	Semi standard non polar	33892256
Chloroprocaine,2TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2698.6	Standard non polar	33892256
Chloroprocaine,2TBDMS,isomer #1	CCN(CC)CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2710.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chloroprocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9i-9400000000-c227313b7fa92099b2dc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloroprocaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9100000000-5a6841e384b0dfbd1238	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 10V, Negative-QTOF	splash10-014i-2590000000-d6a691c88bdf328bdece	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 20V, Negative-QTOF	splash10-0gi0-2960000000-1227ef12643b1bc44f58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 40V, Negative-QTOF	splash10-00di-9800000000-88711037c2b9e1e0a613	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 10V, Negative-QTOF	splash10-014i-0390000000-7684f7020aefa7770440	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 20V, Negative-QTOF	splash10-00fr-1910000000-dc231d66a4743a6fcd82	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 40V, Negative-QTOF	splash10-0059-5900000000-a2436cca9dd4087d6c5b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 10V, Positive-QTOF	splash10-0uk9-1590000000-3e4acb7ab260f903030c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 20V, Positive-QTOF	splash10-0udi-2930000000-1d40bf3d15aab91825f7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 40V, Positive-QTOF	splash10-0umi-8900000000-4f493970e355eb62dd84	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 10V, Positive-QTOF	splash10-00di-0290000000-900e9b454cae510395ba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 20V, Positive-QTOF	splash10-0uk9-0930000000-ede990315b841dc52af0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroprocaine 40V, Positive-QTOF	splash10-0f89-2900000000-89a65d0b933b139cda9f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Chloroprocaine Action Pathway		Not Available

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 DB01161	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01161	21059682	details

Abnormal Concentrations

Not Available

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

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01161

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8293

KEGG Compound ID

C07877

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chloroprocaine

METLIN ID

Not Available

PubChem Compound

8612

PDB ID

Not Available

ChEBI ID

3636

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

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Kuhnert BR, Philipson EH, Pimental R, Kuhnert PM: A prolonged chloroprocaine epidural block in a postpartum patient with abnormal pseudocholinesterase. Anesthesiology. 1982 Jun;56(6):477-8. [PubMed:7081736 ]
Tucker GT, Mather LE: Clinical pharmacokinetics of local anaesthetics. Clin Pharmacokinet. 1979 Jul-Aug;4(4):241-78. [PubMed:385208 ]
Monedero P, Hess P: High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity. Can J Anaesth. 2001 Mar;48(3):318-9. [PubMed:11305839 ]
Smith AR, Hur D, Resano F: Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency. Anesth Analg. 1987 Jul;66(7):677-8. [PubMed:3111302 ]
Raj PP, Ohlweiler D, Hitt BA, Denson DD: Kinetics of local anesthetic esters and the effects of adjuvant drugs on 2-chloroprocaine hydrolysis. Anesthesiology. 1980 Oct;53(4):307-14. [PubMed:7425357 ]

Enzyme Details

2. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Wilcox KM, Paul IA, Ordway GA, Woolverton WL: Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats. Psychopharmacology (Berl). 2001 Sep;157(3):260-8. [PubMed:11605081 ]
Mansbach RS, Jortani SA, Balster RL: Discriminative stimulus effects of esteratic local anesthetics in squirrel monkeys. Eur J Pharmacol. 1995 Feb 14;274(1-3):167-73. [PubMed:7768269 ]
Wilcox KM, Paul IA, Woolverton WL: Comparison between dopamine transporter affinity and self-administration potency of local anesthetics in rhesus monkeys. Eur J Pharmacol. 1999 Feb 19;367(2-3):175-81. [PubMed:10078990 ]
Wilcox KM, Rowlett JK, Paul IA, Ordway GA, Woolverton WL: On the relationship between the dopamine transporter and the reinforcing effects of local anesthetics in rhesus monkeys: practical and theoretical concerns. Psychopharmacology (Berl). 2000 Dec;153(1):139-47. [PubMed:11255924 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 3A

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:: HTR3A
Uniprot ID:: P46098
Molecular weight:: 55279.8

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 ]

Enzyme Details

4. Neuronal acetylcholine receptor subunit alpha-10

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:: CHRNA10
Uniprot ID:: Q9GZZ6
Molecular weight:: 49704.3

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 ]

Enzyme Details

5. Glutamate [NMDA] receptor subunit 3A

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:: GRIN3A
Uniprot ID:: Q8TCU5
Molecular weight:: 125464.1

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 ]

Enzyme Details

6. Sodium channel protein type 10 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

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 ]
Wong K, Strichartz GR, Raymond SA: On the mechanisms of potentiation of local anesthetics by bicarbonate buffer: drug structure-activity studies on isolated peripheral nerve. Anesth Analg. 1993 Jan;76(1):131-43. [PubMed:8418714 ]

Showing metabocard for Chloroprocaine (HMDB0015292)

MOL for HMDB0015292 (Chloroprocaine)

3D MOL for HMDB0015292 (Chloroprocaine)

3D SDF for HMDB0015292 (Chloroprocaine)

3D-SDF for HMDB0015292 (Chloroprocaine)

PDB for HMDB0015292 (Chloroprocaine)

3D PDB for HMDB0015292 (Chloroprocaine)

SMILES for HMDB0015292 (Chloroprocaine)

INCHI for HMDB0015292 (Chloroprocaine)

Structure for HMDB0015292 (Chloroprocaine)

3D Structure for HMDB0015292 (Chloroprocaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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