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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014616

Secondary Accession Numbers

HMDB14616

Metabolite Identification

Common Name

Hexylcaine

Description

Hexylcaine, also known as cyclaine, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Hexylcaine is a drug which is used as a local anesthetic for surface application, infiltration or nerve block. Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. Hexylcaine is a very strong basic compound (based on its pKa).

Structure

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

HMDB0014616
     RDKit          3D
Hexylcaine
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4958    2.3493    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8301    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.2492    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091    0.4930    0.9307 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.0638    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3210    0.7264   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.5942   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144   -0.8524   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5484   -1.6668    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343   -1.4138    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    0.6576    0.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0402    0.0290    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.3864    1.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3199   -0.1723    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631   -0.8130    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5854   -1.0262    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8285   -0.5963   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996    0.0489   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5600    0.2583   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1247    2.6390    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    2.8486    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    2.6729   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    0.4224    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    0.7953   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.8002   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883    0.1215    1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293    0.3525    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    0.0782   -1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    1.7677   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.0692    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.0421   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880   -1.3406   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3263   -0.9024   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9823   -1.3753    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7590   -2.7358    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -1.6644   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -2.0371    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1913   -1.1620    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3971   -1.5380    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8027   -0.7818   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786    0.3914   -2.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664    0.7644   -1.7589 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

473
  Mrv0541 02231214422D          

 19 20  0  0  1  0            999 V2000
    3.0787   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930    1.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    3.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -3.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014616

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3

> <INCHI_KEY>
DKLKMKYDWHYZTD-UHFFFAOYSA-N

> <FORMULA>
C16H23NO2

> <MOLECULAR_WEIGHT>
261.3593

> <EXACT_MASS>
261.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.29060176551161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(cyclohexylamino)propan-2-yl benzoate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.8281649213333333

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.868668944072194

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
76.24070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexylcaine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014616
     RDKit          3D
Hexylcaine
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4958    2.3493    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8301    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.2492    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091    0.4930    0.9307 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.0638    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3210    0.7264   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.5942   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144   -0.8524   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5484   -1.6668    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343   -1.4138    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    0.6576    0.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0402    0.0290    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.3864    1.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3199   -0.1723    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631   -0.8130    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5854   -1.0262    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8285   -0.5963   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996    0.0489   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5600    0.2583   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1247    2.6390    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    2.8486    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    2.6729   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    0.4224    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    0.7953   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.8002   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883    0.1215    1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293    0.3525    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    0.0782   -1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    1.7677   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.0692    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.0421   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880   -1.3406   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3263   -0.9024   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9823   -1.3753    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7590   -2.7358    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -1.6644   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -2.0371    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1913   -1.1620    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3971   -1.5380    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8027   -0.7818   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786    0.3914   -2.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664    0.7644   -1.7589 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 473                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.747  -0.770   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -0.770   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.080   3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.414   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.747   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.414   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.081   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.747   6.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.081   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.080   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.413  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.413  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.413  -6.159   0.000  0.00  0.00           C+0
CONECT    1   11   13                                                       
CONECT    2   13                                                            
CONECT    3    4   10                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    3   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11                                                            
CONECT   13    1    2   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014616
HETATM    1  C1  UNL     1       0.496   2.349   0.889  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.720   0.830   0.864  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.469   0.249   0.111  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.609   0.493   0.931  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.865   0.064   0.450  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.321   0.726  -0.825  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.851   0.594  -0.829  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.214  -0.852  -0.806  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.548  -1.667   0.251  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.034  -1.414   0.249  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.944   0.658   0.165  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.040   0.029   0.731  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.876  -0.386   1.922  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.320  -0.172   0.059  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.363  -0.813   0.703  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.585  -1.026   0.125  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.828  -0.596  -1.161  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.800   0.049  -1.829  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.560   0.258  -1.226  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.125   2.639   1.741  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.482   2.849   0.983  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.067   2.673  -0.099  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.722   0.422   1.877  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.590   0.795  -0.849  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.306  -0.800  -0.150  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.488   0.121   1.904  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.629   0.352   1.233  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.978   0.078  -1.677  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.008   1.768  -0.929  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.212   1.069   0.120  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.301   1.042  -1.736  1.00  0.00           H  
HETATM   32  H13 UNL     1      -5.088  -1.341  -1.794  1.00  0.00           H  
HETATM   33  H14 UNL     1      -6.326  -0.902  -0.601  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.982  -1.375   1.245  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.759  -2.736   0.033  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.702  -1.664  -0.801  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.536  -2.037   1.001  1.00  0.00           H  
HETATM   38  H19 UNL     1       5.191  -1.162   1.722  1.00  0.00           H  
HETATM   39  H20 UNL     1       7.397  -1.538   0.657  1.00  0.00           H  
HETATM   40  H21 UNL     1       7.803  -0.782  -1.580  1.00  0.00           H  
HETATM   41  H22 UNL     1       5.979   0.391  -2.838  1.00  0.00           H  
HETATM   42  H23 UNL     1       3.766   0.764  -1.759  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   11   23
CONECT    3    4   24   25
CONECT    4    5   26
CONECT    5    6   10   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   36   37
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   42
END

HMDB0014616
     RDKit          3D
Hexylcaine
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4958    2.3493    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8301    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.2492    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091    0.4930    0.9307 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.0638    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3210    0.7264   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.5942   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144   -0.8524   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5484   -1.6668    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343   -1.4138    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    0.6576    0.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0402    0.0290    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.3864    1.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3199   -0.1723    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631   -0.8130    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5854   -1.0262    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8285   -0.5963   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996    0.0489   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5600    0.2583   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1247    2.6390    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    2.8486    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    2.6729   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    0.4224    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    0.7953   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.8002   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883    0.1215    1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293    0.3525    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    0.0782   -1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    1.7677   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.0692    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.0421   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880   -1.3406   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3263   -0.9024   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9823   -1.3753    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7590   -2.7358    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -1.6644   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -2.0371    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1913   -1.1620    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3971   -1.5380    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8027   -0.7818   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786    0.3914   -2.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664    0.7644   -1.7589 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cyclaine	HMDB
Hexylcaine hydrochloride	HMDB

Chemical Formula

C₁₆H₂₃NO₂

Average Molecular Weight

261.3593

Monoisotopic Molecular Weight

261.172878985

IUPAC Name

1-(cyclohexylamino)propan-2-yl benzoate

Traditional Name

hexylcaine

CAS Registry Number

532-77-4

SMILES

CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3

InChI Key

DKLKMKYDWHYZTD-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

Benzoate ester
Benzoyl
Cyclohexylamine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:34791 )

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: HMDB0014616)
Membrane (HMDB: HMDB0014616)

Source

Exogenous

Exogenous (HMDB: HMDB0014616)

Process

Not Available

Role

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	0.0097 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0097 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.83	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	9.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76.24 m³·mol⁻¹	ChemAxon
Polarizability	30.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.776	31661259
DarkChem	[M-H]-	161.598	31661259
DeepCCS	[M+H]+	163.82	30932474
DeepCCS	[M-H]-	161.462	30932474
DeepCCS	[M-2H]-	194.413	30932474
DeepCCS	[M+Na]+	169.913	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	166.0	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	166.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.1 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	56.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1942.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	248.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	423.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	428.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	165.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	997.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	414.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1229.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	319.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	30.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexylcaine	CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1	2702.0	Standard polar	33892256
Hexylcaine	CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1	1977.9	Standard non polar	33892256
Hexylcaine	CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1	2049.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexylcaine,1TMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C)OC(=O)C1=CC=CC=C1	2081.1	Semi standard non polar	33892256
Hexylcaine,1TMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C)OC(=O)C1=CC=CC=C1	2096.9	Standard non polar	33892256
Hexylcaine,1TMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C)OC(=O)C1=CC=CC=C1	2761.5	Standard polar	33892256
Hexylcaine,1TBDMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C(C)(C)C)OC(=O)C1=CC=CC=C1	2333.5	Semi standard non polar	33892256
Hexylcaine,1TBDMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C(C)(C)C)OC(=O)C1=CC=CC=C1	2279.8	Standard non polar	33892256
Hexylcaine,1TBDMS,isomer #1	CC(CN(C1CCCCC1)[Si](C)(C)C(C)(C)C)OC(=O)C1=CC=CC=C1	2871.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hexylcaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4910000000-9d078efa75ea2644f15d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexylcaine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 10V, Positive-QTOF	splash10-03dl-0960000000-666d132f25224cb4333c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 20V, Positive-QTOF	splash10-0006-5910000000-4a781f8df0db63e247e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 40V, Positive-QTOF	splash10-0a59-9700000000-8f61edaf2f38ba400b93	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 10V, Negative-QTOF	splash10-03di-2980000000-176aaf9d71a17be5212a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 20V, Negative-QTOF	splash10-03fs-9770000000-50ea7352357a250316ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 40V, Negative-QTOF	splash10-05bb-9400000000-133ae6248b75f916d084	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 10V, Negative-QTOF	splash10-03di-0190000000-058708c045dbe4130aaa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 20V, Negative-QTOF	splash10-03mi-3950000000-192fa2b22b06abc093c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 40V, Negative-QTOF	splash10-004i-9100000000-48021f84a4b8fbb807a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 10V, Positive-QTOF	splash10-03dl-2980000000-0bf7df762ecb94eaee9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 20V, Positive-QTOF	splash10-0a4i-9410000000-862fcbfa2afb55740139	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexylcaine 40V, Positive-QTOF	splash10-0a4i-9420000000-f82fc7a14b4f6baa0c76	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00473	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00473	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00473

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10315

KEGG Compound ID

C14172

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexylcaine

METLIN ID

Not Available

PubChem Compound

10770

PDB ID

Not Available

ChEBI ID

309162

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 ]

Enzyme Details

2. 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 ]

Showing metabocard for Hexylcaine (HMDB0014616)

MOL for HMDB0014616 (Hexylcaine)

3D MOL for HMDB0014616 (Hexylcaine)

3D SDF for HMDB0014616 (Hexylcaine)

3D-SDF for HMDB0014616 (Hexylcaine)

PDB for HMDB0014616 (Hexylcaine)

3D PDB for HMDB0014616 (Hexylcaine)

SMILES for HMDB0014616 (Hexylcaine)

INCHI for HMDB0014616 (Hexylcaine)

Structure for HMDB0014616 (Hexylcaine)

3D Structure for HMDB0014616 (Hexylcaine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References