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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 02:51:48 UTC

HMDB ID

HMDB0014945

Secondary Accession Numbers

HMDB14945

Metabolite Identification

Common Name

Proparacaine

Description

Proparacaine is only found in individuals that have used or taken this drug. It is a topical anesthetic drug of the amino ester group. It is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. [Wikipedia ]The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.

Structure

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

HMDB0014945
     RDKit          3D
Proparacaine
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.0082   -1.0510   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372   -0.7142   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2829    0.5294    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341    0.5782    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    0.5894    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.5555   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568    0.5738   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.6281    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5170    0.6455    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.6116   -1.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    0.6968    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.7081    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -0.4803    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.3433    0.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -1.3873   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1409   -1.5313   -1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    0.9483    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0004    1.8313   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    0.6643    1.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449    0.6461    1.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    0.6849    3.0673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033   -1.8328   -1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.1841   -2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0409   -1.5081   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5887   -1.5806    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8300   -0.6436   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6039    1.4349   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0039    0.5863    1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7494    0.5293   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    0.5437   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    0.7710    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255    1.6406    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.3582    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162   -0.7348   -0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5308   -1.2470   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1947   -2.3499    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -1.7001   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -2.4458   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -0.6536   -2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9477    1.4852    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090    0.8602    0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    1.4956   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123    1.9759   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    2.8845   -0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    0.7093    2.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091   -0.1908    3.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888    1.5947    3.5528 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
M  END

807
  Mrv0541 02231215012D          

 21 21  0  0  0  0            999 V2000
    6.6515   -0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.9659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.9034    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
    1.6500    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2 14  1  0  0  0  0
  2 18  1  0  0  0  0
  3 13  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 15  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
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014945

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3

> <INCHI_KEY>
KCLANYCVBBTKTO-UHFFFAOYSA-N

> <FORMULA>
C16H26N2O3

> <MOLECULAR_WEIGHT>
294.3892

> <EXACT_MASS>
294.194342708

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.00077680123866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.601716341666667

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.961552253097953

> <JCHEM_POLAR_SURFACE_AREA>
64.79

> <JCHEM_REFRACTIVITY>
86.03580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proparacaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014945
     RDKit          3D
Proparacaine
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.0082   -1.0510   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372   -0.7142   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2829    0.5294    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341    0.5782    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    0.5894    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.5555   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568    0.5738   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.6281    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5170    0.6455    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.6116   -1.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    0.6968    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.7081    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -0.4803    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.3433    0.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -1.3873   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1409   -1.5313   -1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    0.9483    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0004    1.8313   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    0.6643    1.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449    0.6461    1.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    0.6849    3.0673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033   -1.8328   -1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.1841   -2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0409   -1.5081   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5887   -1.5806    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8300   -0.6436   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6039    1.4349   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0039    0.5863    1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7494    0.5293   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    0.5437   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    0.7710    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255    1.6406    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.3582    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162   -0.7348   -0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5308   -1.2470   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1947   -2.3499    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -1.7001   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -2.4458   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -0.6536   -2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9477    1.4852    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090    0.8602    0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    1.4956   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123    1.9759   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    2.8845   -0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    0.7093    2.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091   -0.1908    3.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888    1.5947    3.5528 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 807                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.416  -0.624   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   3.996   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.750   1.686   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      15.083  -3.704   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.748   5.536   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.750  -2.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.083  -5.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.417  -2.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.750  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.417  -6.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.751  -3.704   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   1.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416   0.916   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   3.226   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   3.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   3.226   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   0.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   3.226   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   1.686   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414   3.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   3.226   0.000  0.00  0.00           C+0
CONECT    1    9   13                                                       
CONECT    2   14   18                                                       
CONECT    3   13                                                            
CONECT    4    6    7    8                                                  
CONECT    5   15                                                            
CONECT    6    4    9                                                       
CONECT    7    4   10                                                       
CONECT    8    4   11                                                       
CONECT    9    1    6                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12   13   16   17                                                  
CONECT   13    1    3   12                                                  
CONECT   14    2   15   19                                                  
CONECT   15    5   14   16                                                  
CONECT   16   12   15                                                       
CONECT   17   12   19                                                       
CONECT   18    2   20                                                       
CONECT   19   14   17                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0014945
HETATM    1  C1  UNL     1      -6.008  -1.051  -1.464  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.737  -0.714  -0.210  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.283   0.529   0.512  1.00  0.00           C  
HETATM    4  O1  UNL     1      -5.034   0.578   0.946  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.739   0.589   0.670  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.140   0.556  -0.570  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.757   0.574  -0.741  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.927   0.628   0.343  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.517   0.645   0.168  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.987   0.612  -1.000  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.402   0.697   1.220  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.775   0.708   1.013  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.347  -0.480   0.316  1.00  0.00           C  
HETATM   14  N1  UNL     1       4.749  -0.343   0.172  1.00  0.00           N  
HETATM   15  C11 UNL     1       5.440  -1.387  -0.476  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.141  -1.531  -1.942  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.306   0.948   0.175  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.000   1.831  -0.984  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.481   0.664   1.596  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.845   0.646   1.771  1.00  0.00           C  
HETATM   21  N2  UNL     1      -3.400   0.685   3.067  1.00  0.00           N  
HETATM   22  H1  UNL     1      -6.603  -1.833  -1.988  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.952  -0.184  -2.151  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.041  -1.508  -1.232  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.589  -1.581   0.492  1.00  0.00           H  
HETATM   26  H5  UNL     1      -7.830  -0.644  -0.452  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.604   1.435  -0.104  1.00  0.00           H  
HETATM   28  H7  UNL     1      -7.004   0.586   1.410  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.749   0.529  -1.456  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.366   0.544  -1.759  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.264   0.771   2.028  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.025   1.641   0.460  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.183  -1.358   1.013  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.816  -0.735  -0.618  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.531  -1.247  -0.351  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.195  -2.350   0.016  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.065  -1.700  -2.087  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.683  -2.446  -2.296  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.494  -0.654  -2.492  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.948   1.485   1.103  1.00  0.00           H  
HETATM   41  H20 UNL     1       6.409   0.860   0.259  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.189   1.496  -1.637  1.00  0.00           H  
HETATM   43  H22 UNL     1       5.912   1.976  -1.634  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.746   2.884  -0.661  1.00  0.00           H  
HETATM   45  H24 UNL     1      -0.838   0.709   2.489  1.00  0.00           H  
HETATM   46  H25 UNL     1      -3.709  -0.191   3.513  1.00  0.00           H  
HETATM   47  H26 UNL     1      -3.489   1.595   3.553  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5
CONECT    5    6    6   20
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   19
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   17
CONECT   15   16   35   36
CONECT   16   37   38   39
CONECT   17   18   40   41
CONECT   18   42   43   44
CONECT   19   20   20   45
CONECT   20   21
CONECT   21   46   47
END

HMDB0014945
     RDKit          3D
Proparacaine
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.0082   -1.0510   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372   -0.7142   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2829    0.5294    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341    0.5782    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    0.5894    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.5555   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568    0.5738   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.6281    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5170    0.6455    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.6116   -1.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    0.6968    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.7081    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -0.4803    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.3433    0.1721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -1.3873   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1409   -1.5313   -1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    0.9483    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0004    1.8313   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    0.6643    1.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449    0.6461    1.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    0.6849    3.0673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033   -1.8328   -1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -0.1841   -2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0409   -1.5081   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5887   -1.5806    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8300   -0.6436   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6039    1.4349   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0039    0.5863    1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7494    0.5293   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    0.5437   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    0.7710    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255    1.6406    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.3582    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162   -0.7348   -0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5308   -1.2470   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1947   -2.3499    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -1.7001   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -2.4458   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -0.6536   -2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9477    1.4852    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090    0.8602    0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    1.4956   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123    1.9759   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    2.8845   -0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    0.7093    2.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091   -0.1908    3.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888    1.5947    3.5528 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Proxymetacaine	Kegg
Prossimetacaina	HMDB
Proximetacainum	HMDB
Ophthetic	HMDB
Parcaine	HMDB
Alcaine	HMDB
Ocu-caine	HMDB
Proxymetacaine hydrochloride	HMDB
AK-taine	HMDB
Kainair	HMDB
Proxymethacaine	HMDB
Chibro-kerakain	HMDB
Kéracaine	HMDB
Minims proxymetacaine hydrochloride	HMDB
Ophthaine	HMDB
Proparakain-pos	HMDB
Proxymetacaine monohydrochloride	HMDB
Proparacaine hydrochloride	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochloride	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride*benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride	HMDB
Proparacaine HCL	HMDB

Chemical Formula

C₁₆H₂₆N₂O₃

Average Molecular Weight

294.3892

Monoisotopic Molecular Weight

294.194342708

IUPAC Name

2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

Traditional Name

proparacaine

CAS Registry Number

499-67-2

SMILES

CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC

InChI Identifier

InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3

InChI Key

KCLANYCVBBTKTO-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
Aminophenyl ether
Phenoxy compound
Benzoyl
Aniline or substituted anilines
Phenol ether
Alkyl aryl ether
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:8485 )

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

Extracellular (HMDB: HMDB0014945)
Membrane (HMDB: HMDB0014945)

Source

Exogenous

Exogenous (HMDB: HMDB0014945)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Proparacaine Pathway (HMDB: HMDB0014945)
Proparacaine Action Pathway (PathBank: SMP0000403)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 183.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.39 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.04 m³·mol⁻¹	ChemAxon
Polarizability	34 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]+	169.124	31661259
DarkChem	[M-H]-	166.688	31661259
DeepCCS	[M+H]+	173.995	30932474
DeepCCS	[M-H]-	171.637	30932474
DeepCCS	[M-2H]-	204.522	30932474
DeepCCS	[M+Na]+	180.088	30932474
AllCCS	[M+H]+	172.2	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	173.7	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Proparacaine	CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC	3469.6	Standard polar	33892256
Proparacaine	CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC	2366.1	Standard non polar	33892256
Proparacaine	CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC	2370.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Proparacaine,1TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C	2491.7	Semi standard non polar	33892256
Proparacaine,1TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C	2428.6	Standard non polar	33892256
Proparacaine,1TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C	2996.0	Standard polar	33892256
Proparacaine,2TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C	2428.0	Semi standard non polar	33892256
Proparacaine,2TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C	2431.9	Standard non polar	33892256
Proparacaine,2TMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C	2766.3	Standard polar	33892256
Proparacaine,1TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C	2670.1	Semi standard non polar	33892256
Proparacaine,1TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C	2658.9	Standard non polar	33892256
Proparacaine,1TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C	3073.1	Standard polar	33892256
Proparacaine,2TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2818.0	Semi standard non polar	33892256
Proparacaine,2TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2818.9	Standard non polar	33892256
Proparacaine,2TBDMS,isomer #1	CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2951.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Proparacaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9320000000-1725fcdf405f1285cf5f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proparacaine 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 - Proparacaine , positive-QTOF	splash10-0f6t-0590000000-0aae7080739b3c83b4a4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 10V, Positive-QTOF	splash10-0f92-3790000000-19484885f2060a30ee39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 20V, Positive-QTOF	splash10-0udl-6940000000-b6eb0be7d6e42c79f6d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 40V, Positive-QTOF	splash10-0006-9300000000-8b40ab2bb2e6ca190ac6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 10V, Negative-QTOF	splash10-0006-2490000000-e0dd5d94666e639cd15f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 20V, Negative-QTOF	splash10-0udl-3890000000-83f45f2c670646cf13b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 40V, Negative-QTOF	splash10-0a4i-4910000000-080bada57e1dc3ab313c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 10V, Positive-QTOF	splash10-0udi-0940000000-dd6bde08618373162607	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 20V, Positive-QTOF	splash10-0udi-2950000000-6cf937b31cea35f9327a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 40V, Positive-QTOF	splash10-0udr-2900000000-74d2433c695036dfb8f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 10V, Negative-QTOF	splash10-0006-0490000000-6934514b2f05a7f1e043	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 20V, Negative-QTOF	splash10-0udj-2930000000-d9841e3d4745b761afc5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proparacaine 40V, Negative-QTOF	splash10-0zg0-0900000000-acfb0c0e342bd2f577c8	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Proparacaine 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 DB00807	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00807	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

DB00807

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4766

KEGG Compound ID

C07383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Proxymetacaine

METLIN ID

Not Available

PubChem Compound

4935

PDB ID

Not Available

ChEBI ID

309007

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 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 ]
Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. [PubMed:9476974 ]

Showing metabocard for Proparacaine (HMDB0014945)

MOL for HMDB0014945 (Proparacaine)

3D MOL for HMDB0014945 (Proparacaine)

3D SDF for HMDB0014945 (Proparacaine)

3D-SDF for HMDB0014945 (Proparacaine)

PDB for HMDB0014945 (Proparacaine)

3D PDB for HMDB0014945 (Proparacaine)

SMILES for HMDB0014945 (Proparacaine)

INCHI for HMDB0014945 (Proparacaine)

Structure for HMDB0014945 (Proparacaine)

3D Structure for HMDB0014945 (Proparacaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References