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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014888

Secondary Accession Numbers

HMDB14888

Metabolite Identification

Common Name

Prilocaine

Description

Prilocaine is only found in individuals that have used or taken this drug. It is a local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)Prilocaine acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.

Structure

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

HMDB0014888
     RDKit          3D
Prilocaine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.5220   -0.2527    2.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377   -1.0661    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951   -0.5003   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -0.4798    0.4265 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3058    0.0477   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -0.8358   -1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857   -0.0732    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1413   -0.5971    1.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    0.3953   -0.6762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    0.3426   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.1775    0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.2051    1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1818    0.3146    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7738    0.8378   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559    0.8710   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.4344   -2.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5134   -0.4324    2.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -0.5417    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    0.8317    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559   -1.0427    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -2.1029    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.2370   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9282    0.4478   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327   -0.0041    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895    1.0736   -0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0889   -1.8906   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.4902   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -0.6962   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.8141   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.5859    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.6199    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    0.3044    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983    1.2554   -1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    0.6735   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    2.2167   -2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    1.9708   -2.9062 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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  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  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

750
  Mrv0541 02231214582D          

 16 16  0  0  1  0            999 V2000
    4.5080   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014888

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCNC(C)C(=O)NC1=CC=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)

> <INCHI_KEY>
MVFGUOIZUNYYSO-UHFFFAOYSA-N

> <FORMULA>
C13H20N2O

> <MOLECULAR_WEIGHT>
220.3107

> <EXACT_MASS>
220.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.976297247961284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2-methylphenyl)-2-(propylamino)propanamide

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.6809227156666666

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.509081505542508

> <JCHEM_PKA_STRONGEST_BASIC>
8.815906516402368

> <JCHEM_POLAR_SURFACE_AREA>
41.13

> <JCHEM_REFRACTIVITY>
67.86300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prilocaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014888
     RDKit          3D
Prilocaine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.5220   -0.2527    2.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377   -1.0661    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951   -0.5003   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -0.4798    0.4265 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3058    0.0477   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -0.8358   -1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857   -0.0732    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1413   -0.5971    1.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    0.3953   -0.6762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    0.3426   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.1775    0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.2051    1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1818    0.3146    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7738    0.8378   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559    0.8710   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.4344   -2.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5134   -0.4324    2.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -0.5417    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    0.8317    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559   -1.0427    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -2.1029    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.2370   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9282    0.4478   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327   -0.0041    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895    1.0736   -0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0889   -1.8906   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.4902   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -0.6962   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.8141   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.5859    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.6199    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    0.3044    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983    1.2554   -1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    0.6735   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    2.2167   -2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    1.9708   -2.9062 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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  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  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 750                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -1.155   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.415   1.925   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748  -1.155   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   5.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -5.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -5.775   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    4    5                                                       
CONECT    3    7    9                                                       
CONECT    4    2    7    8                                                  
CONECT    5    2    6                                                       
CONECT    6    5   11                                                       
CONECT    7    1    3    4                                                  
CONECT    8    4                                                            
CONECT    9    3   10   12                                                  
CONECT   10    9   13   14                                                  
CONECT   11    6                                                            
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   10                                                            
CONECT   15   12   16                                                       
CONECT   16   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0014888
HETATM    1  C1  UNL     1       4.522  -0.253   2.253  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.538  -1.066   0.978  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.595  -0.500  -0.053  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.227  -0.480   0.427  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.306   0.048  -0.518  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.281  -0.836  -1.772  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.086  -0.073   0.071  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.141  -0.597   1.207  1.00  0.00           O  
HETATM    9  N2  UNL     1      -1.172   0.395  -0.676  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.515   0.343  -0.248  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.934  -0.177   0.955  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.277  -0.205   1.327  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.182   0.315   0.434  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.774   0.838  -0.773  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.456   0.871  -1.151  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.019   1.434  -2.452  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.513  -0.432   2.743  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.708  -0.542   2.924  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.523   0.832   1.983  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.556  -1.043   0.545  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.197  -2.103   1.210  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.599  -1.237  -0.910  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.928   0.448  -0.478  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.133  -0.004   1.347  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.489   1.074  -0.841  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.089  -1.891  -1.493  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.430  -0.490  -2.386  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.189  -0.696  -2.372  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.929   0.814  -1.626  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.243  -0.586   1.662  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.591  -0.620   2.282  1.00  0.00           H  
HETATM   32  H16 UNL     1      -6.232   0.304   0.700  1.00  0.00           H  
HETATM   33  H17 UNL     1      -5.498   1.255  -1.491  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.647   0.674  -3.146  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.233   2.217  -2.324  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.893   1.971  -2.906  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24
CONECT    5    6    7   25
CONECT    6   26   27   28
CONECT    7    8    8    9
CONECT    9   10   29
CONECT   10   11   11   15
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16
CONECT   16   34   35   36
END

HMDB0014888
     RDKit          3D
Prilocaine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.5220   -0.2527    2.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377   -1.0661    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951   -0.5003   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -0.4798    0.4265 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3058    0.0477   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -0.8358   -1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857   -0.0732    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1413   -0.5971    1.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722    0.3953   -0.6762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    0.3426   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.1775    0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.2051    1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1818    0.3146    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7738    0.8378   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559    0.8710   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.4344   -2.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5134   -0.4324    2.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -0.5417    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    0.8317    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559   -1.0427    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -2.1029    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.2370   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9282    0.4478   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327   -0.0041    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895    1.0736   -0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0889   -1.8906   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.4902   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -0.6962   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.8141   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.5859    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.6199    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    0.3044    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983    1.2554   -1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    0.6735   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    2.2167   -2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    1.9708   -2.9062 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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  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  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Propylamino)-O-propionotoluidide	ChEBI
2-Methyl-alpha-propylaminopropionanilide	ChEBI
alpha-N-Propylamino-2-methylpropionanilide	ChEBI
N-(2-Methylphenyl)-2-(propylamino)propanamide	ChEBI
O-Methyl-2-propylaminopropionanilide	ChEBI
O-Methyl-alpha-propylaminopropionanilide	ChEBI
Prilocaina	ChEBI
Prilocaine base	ChEBI
Prilocainum	ChEBI
Propitocaine	ChEBI
2-Methyl-a-propylaminopropionanilide	Generator
2-Methyl-α-propylaminopropionanilide	Generator
a-N-Propylamino-2-methylpropionanilide	Generator
Α-N-propylamino-2-methylpropionanilide	Generator
O-Methyl-a-propylaminopropionanilide	Generator
O-Methyl-α-propylaminopropionanilide	Generator
Astra brand OF prilocaine hydrochloride	HMDB
Citanest octapressin	HMDB
Parnell brand OF prilocaine hydrochloride	HMDB
Delvet brand OF prilocaine hydrochloride	HMDB
Prilocaine hydrochloride	HMDB
Xylonest	HMDB
Inibsa brand OF prilocaine hydrochloride	HMDB
AstraZeneca brand OF prilocaine hydrochloride	HMDB
Citanest	HMDB

Chemical Formula

C₁₃H₂₀N₂O

Average Molecular Weight

220.3107

Monoisotopic Molecular Weight

220.157563272

IUPAC Name

N-(2-methylphenyl)-2-(propylamino)propanamide

Traditional Name

prilocaine

CAS Registry Number

721-50-6

SMILES

CCCNC(C)C(=O)NC1=CC=CC=C1C

InChI Identifier

InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)

InChI Key

MVFGUOIZUNYYSO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Alanine or derivatives
Anilide
N-arylamide
Toluene
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:8404 )
amino acid amide (CHEBI:8404 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014888)

Source

Exogenous

Exogenous (HMDB: HMDB0014888)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Prilocaine Action Pathway (PathBank: SMP0000401)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	37 - 38 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.33 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	154.25	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001289

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	1.87	ALOGPS
logP	2.68	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.51	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.86 m³·mol⁻¹	ChemAxon
Polarizability	25.98 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
DarkChem	[M+H]+	152.529	31661259
DarkChem	[M-H]-	148.282	31661259
DeepCCS	[M+H]+	153.865	30932474
DeepCCS	[M-H]-	151.507	30932474
DeepCCS	[M-2H]-	185.698	30932474
DeepCCS	[M+Na]+	160.912	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	150.0	32859911
AllCCS	[M+NH4]+	157.1	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	156.2	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prilocaine	CCCNC(C)C(=O)NC1=CC=CC=C1C	2357.9	Standard polar	33892256
Prilocaine	CCCNC(C)C(=O)NC1=CC=CC=C1C	1820.1	Standard non polar	33892256
Prilocaine	CCCNC(C)C(=O)NC1=CC=CC=C1C	1843.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prilocaine,1TMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C	1926.9	Semi standard non polar	33892256
Prilocaine,1TMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C	1886.8	Standard non polar	33892256
Prilocaine,1TMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C	2451.4	Standard polar	33892256
Prilocaine,1TMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C	1735.1	Semi standard non polar	33892256
Prilocaine,1TMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C	1787.7	Standard non polar	33892256
Prilocaine,1TMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C	2182.0	Standard polar	33892256
Prilocaine,2TMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C)[Si](C)(C)C	1897.1	Semi standard non polar	33892256
Prilocaine,2TMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C)[Si](C)(C)C	1920.7	Standard non polar	33892256
Prilocaine,2TMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C)[Si](C)(C)C	2154.6	Standard polar	33892256
Prilocaine,1TBDMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	2185.2	Semi standard non polar	33892256
Prilocaine,1TBDMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	2082.7	Standard non polar	33892256
Prilocaine,1TBDMS,isomer #1	CCCN(C(C)C(=O)NC1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	2552.4	Standard polar	33892256
Prilocaine,1TBDMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	1969.2	Semi standard non polar	33892256
Prilocaine,1TBDMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	2014.3	Standard non polar	33892256
Prilocaine,1TBDMS,isomer #2	CCCNC(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C	2314.3	Standard polar	33892256
Prilocaine,2TBDMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2375.5	Semi standard non polar	33892256
Prilocaine,2TBDMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2336.1	Standard non polar	33892256
Prilocaine,2TBDMS,isomer #1	CCCN(C(C)C(=O)N(C1=CC=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2410.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prilocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-c7980348fde318ec4477	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prilocaine 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 - Prilocaine LC-ESI-qTof , Positive-QTOF	splash10-00di-1390000000-c8416e476741832b2637	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-qTof , Positive-QTOF	splash10-00di-0290000000-ecb70add14abedae843c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-qTof , Positive-QTOF	splash10-00di-0290000000-44d4259708c3f68cf9fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9010000000-62668ab56142315d25c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-b24ca970640547e77f45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-fa235236a550137d65ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-c5326a5261240ae38b1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-6c794305d6cd738a7fa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine LC-ESI-QFT , positive-QTOF	splash10-000i-9000000000-ee81ed4cf795affc96e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine , positive-QTOF	splash10-00di-0290000000-ecb70add14abedae843c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine , positive-QTOF	splash10-00di-0290000000-44d4259708c3f68cf9fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine , positive-QTOF	splash10-00di-1390000000-c8416e476741832b2637	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 30V, Positive-QTOF	splash10-000i-9000000000-b24ca970640547e77f45	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 15V, Positive-QTOF	splash10-000i-9010000000-b031f8cfcb2f5d925055	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 45V, Positive-QTOF	splash10-000i-9000000000-2f951b718ec1c3fb96b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 60V, Positive-QTOF	splash10-000i-9000000000-2e40656cee28569c9534	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 90V, Positive-QTOF	splash10-000i-9000000000-29bc00afaed4a8f65110	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prilocaine 75V, Positive-QTOF	splash10-000i-9000000000-439134ebdf51577dd841	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 10V, Positive-QTOF	splash10-0abi-9760000000-6466db752ba0441390c8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 20V, Positive-QTOF	splash10-0a4u-9400000000-cf766fd99bb51d64aaac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 40V, Positive-QTOF	splash10-0006-9100000000-c417e9eda43debe8e2cb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 10V, Negative-QTOF	splash10-014i-0290000000-c8d33031e7de066c46c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 20V, Negative-QTOF	splash10-0cdi-1940000000-30003dbb848dad517df1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 40V, Negative-QTOF	splash10-0pbc-9800000000-4573f7687d90e96645b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prilocaine 10V, Positive-QTOF	splash10-000i-9110000000-d2d37df22d6946b4ebee	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Prilocaine 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 DB00750	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00750	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00750

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4737

KEGG Compound ID

C07531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prilocaine

METLIN ID

Not Available

PubChem Compound

4906

PDB ID

Not Available

ChEBI ID

8404

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. Sodium channel protein type 5 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 Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Prilocaine (HMDB0014888)

MOL for HMDB0014888 (Prilocaine)

3D MOL for HMDB0014888 (Prilocaine)

3D SDF for HMDB0014888 (Prilocaine)

3D-SDF for HMDB0014888 (Prilocaine)

PDB for HMDB0014888 (Prilocaine)

3D PDB for HMDB0014888 (Prilocaine)

SMILES for HMDB0014888 (Prilocaine)

INCHI for HMDB0014888 (Prilocaine)

Structure for HMDB0014888 (Prilocaine)

3D Structure for HMDB0014888 (Prilocaine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References