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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:55:18 UTC

Update Date

2021-09-14 14:58:08 UTC

HMDB ID

HMDB0060725

Secondary Accession Numbers

HMDB60725

Metabolite Identification

Common Name

2,6-Pipecoloxylidide

Description

2,6-Pipecoloxylidide, also known as desbutylbupivacaine or pipecolylxylidine-2',6', belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 2,6-Pipecoloxylidide is a very strong basic compound (based on its pKa). 2,6-Pipecoloxylidide is a metabolite of bupivacaine. It is commonly marketed under various trade names, including Marcain, Marcaine (CareStream Dental), Sensorcaine (Astra Zeneca) and Vivacaine (Septodont). Bupivacaine is a local anaesthetic drug belonging to the amino amide group.

Structure

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

HMDB0060725
     RDKit          3D
2,6-Pipecoloxylidide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.2692   -2.1721    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.8747    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1401   -0.7660    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    0.4587   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    1.5591   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    1.4164   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863    2.5381   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    0.2127    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.0793    0.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.6844   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637   -1.3642   -1.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -0.8882    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892   -0.1093    1.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.9616    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742    0.3591    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599   -0.6112   -0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -0.4829   -1.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -2.8926    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5715    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -2.0880    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -1.5987    0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632    0.5438   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1287    2.5225   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    2.6753    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    2.3806   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    3.4840   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -2.2139   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.9872    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.4170    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428   -0.8113    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4386    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176    1.7221    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -0.1392    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7996    1.1874   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3054   -0.5398   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9320   -1.6363   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648    0.4753   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END


  Mrv0541 07041311552D          

 17 18  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  4  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060725

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC(C)=C1N=C(O)C1CCCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)

> <INCHI_KEY>
SILRCGDPZGQJOQ-UHFFFAOYSA-N

> <FORMULA>
C14H20N2O

> <MOLECULAR_WEIGHT>
232.3214

> <EXACT_MASS>
232.157563272

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.768268996350976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.4846274966884112

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.083008803939035

> <JCHEM_PKA_STRONGEST_BASIC>
8.80076701895956

> <JCHEM_POLAR_SURFACE_AREA>
44.620000000000005

> <JCHEM_REFRACTIVITY>
71.78010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060725
     RDKit          3D
2,6-Pipecoloxylidide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.2692   -2.1721    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.8747    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1401   -0.7660    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    0.4587   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    1.5591   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    1.4164   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863    2.5381   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    0.2127    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.0793    0.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.6844   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637   -1.3642   -1.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -0.8882    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892   -0.1093    1.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.9616    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742    0.3591    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599   -0.6112   -0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -0.4829   -1.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -2.8926    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5715    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -2.0880    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -1.5987    0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632    0.5438   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1287    2.5225   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    2.6753    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    2.3806   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    3.4840   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -2.2139   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.9872    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.4170    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428   -0.8113    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4386    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176    1.7221    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -0.1392    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7996    1.1874   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3054   -0.5398   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9320   -1.6363   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648    0.4753   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.002   6.160   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       5.335   9.240   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    3   12                                                       
CONECT    9    4   15                                                       
CONECT   10    1    6   13                                                  
CONECT   11    2    7   13                                                  
CONECT   12    8   14   15                                                  
CONECT   13   10   11   16                                                  
CONECT   14   12   16   17                                                  
CONECT   15    9   12                                                       
CONECT   16   13   14                                                       
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0060725
HETATM    1  C1  UNL     1      -2.269  -2.172   0.952  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.786  -0.875   0.472  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.140  -0.766   0.156  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.620   0.459  -0.295  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.801   1.559  -0.438  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.448   1.416  -0.112  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.486   2.538  -0.230  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.946   0.213   0.338  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.568   0.079   0.667  1.00  0.00           N  
HETATM   10  C9  UNL     1       0.164  -0.684  -0.073  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.364  -1.364  -1.165  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.618  -0.888   0.190  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.089  -0.109   1.391  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.093   0.962   0.982  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.274   0.359   0.257  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.760  -0.611  -0.775  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.338  -0.483  -1.008  1.00  0.00           N  
HETATM   18  H1  UNL     1      -2.280  -2.893   0.110  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.930  -2.571   1.752  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.263  -2.088   1.369  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.815  -1.599   0.252  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.663   0.544  -0.540  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.129   2.522  -0.782  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.885   2.675   0.715  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.752   2.381  -1.040  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.059   3.484  -0.344  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.037  -2.214  -1.509  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.760  -1.987   0.310  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.265   0.417   1.912  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.643  -0.811   2.049  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.473   1.439   1.895  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.618   1.722   0.325  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.971  -0.139   0.982  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.800   1.187  -0.268  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.305  -0.540  -1.724  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.932  -1.636  -0.378  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.065   0.475  -1.318  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    8
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   23
CONECT    6    7    8    8
CONECT    7   24   25   26
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   17   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   37
END

HMDB0060725
     RDKit          3D
2,6-Pipecoloxylidide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.2692   -2.1721    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.8747    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1401   -0.7660    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    0.4587   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    1.5591   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    1.4164   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863    2.5381   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    0.2127    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.0793    0.6670 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.6844   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637   -1.3642   -1.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -0.8882    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892   -0.1093    1.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.9616    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742    0.3591    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599   -0.6112   -0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -0.4829   -1.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -2.8926    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5715    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -2.0880    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -1.5987    0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632    0.5438   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1287    2.5225   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    2.6753    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    2.3806   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    3.4840   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -2.2139   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.9872    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.4170    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428   -0.8113    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4386    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176    1.7221    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -0.1392    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7996    1.1874   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3054   -0.5398   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9320   -1.6363   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648    0.4753   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',6'-Pipecoloxylidide	HMDB
2',6'-Pipecoloxylidide, (-)-isomer	HMDB
2',6'-Pipecoloxylidide, monoacetate, (R)-isomer	HMDB
Desbutylbupivacaine	HMDB
Pipecolylxylidine-2',6'	HMDB
2',6'-Pipecoloxylidide, (+)-isomer	HMDB
2',6'-Pipecoloxylidide, (R)-isomer	HMDB
2',6'-Pipecoloxylidide, 14C-labeled	HMDB

Chemical Formula

C₁₄H₂₀N₂O

Average Molecular Weight

232.3214

Monoisotopic Molecular Weight

232.157563272

IUPAC Name

N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid

Traditional Name

N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC1=CC=CC(C)=C1N=C(O)C1CCCCN1

InChI Identifier

InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)

InChI Key

SILRCGDPZGQJOQ-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
2-piperidinecarboxamide
Piperidinecarboxamide
Anilide
M-xylene
Xylene
N-arylamide
Monocyclic benzene moiety
Piperidine
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Secondary aliphatic amine
Azacycle
Secondary amine
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060725)
Liver (HMDB: HMDB0060725)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060725)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060725)

Cellular substructure

Cytoplasm (HMDB: HMDB0060725)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	1.82	ALOGPS
logP	1.48	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	5.08	ChemAxon
pKa (Strongest Basic)	8.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.78 m³·mol⁻¹	ChemAxon
Polarizability	26.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.391	31661259
DarkChem	[M-H]-	149.244	31661259
DeepCCS	[M+H]+	151.976	30932474
DeepCCS	[M-H]-	149.618	30932474
DeepCCS	[M-2H]-	183.2	30932474
DeepCCS	[M+Na]+	158.079	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Pipecoloxylidide	CC1=CC=CC(C)=C1N=C(O)C1CCCCN1	2416.9	Standard polar	33892256
2,6-Pipecoloxylidide	CC1=CC=CC(C)=C1N=C(O)C1CCCCN1	2013.7	Standard non polar	33892256
2,6-Pipecoloxylidide	CC1=CC=CC(C)=C1N=C(O)C1CCCCN1	2003.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Pipecoloxylidide,1TMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C)C1CCCCN1	1973.7	Semi standard non polar	33892256
2,6-Pipecoloxylidide,1TMS,isomer #2	CC1=CC=CC(C)=C1N=C(O)C1CCCCN1[Si](C)(C)C	1984.7	Semi standard non polar	33892256
2,6-Pipecoloxylidide,2TMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C)C1CCCCN1[Si](C)(C)C	2013.3	Semi standard non polar	33892256
2,6-Pipecoloxylidide,2TMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C)C1CCCCN1[Si](C)(C)C	2070.7	Standard non polar	33892256
2,6-Pipecoloxylidide,2TMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C)C1CCCCN1[Si](C)(C)C	2692.1	Standard polar	33892256
2,6-Pipecoloxylidide,1TBDMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C(C)(C)C)C1CCCCN1	2160.7	Semi standard non polar	33892256
2,6-Pipecoloxylidide,1TBDMS,isomer #2	CC1=CC=CC(C)=C1N=C(O)C1CCCCN1[Si](C)(C)C(C)(C)C	2180.3	Semi standard non polar	33892256
2,6-Pipecoloxylidide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C(C)(C)C)C1CCCCN1[Si](C)(C)C(C)(C)C	2419.8	Semi standard non polar	33892256
2,6-Pipecoloxylidide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C(C)(C)C)C1CCCCN1[Si](C)(C)C(C)(C)C	2436.8	Standard non polar	33892256
2,6-Pipecoloxylidide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N=C(O[Si](C)(C)C(C)(C)C)C1CCCCN1[Si](C)(C)C(C)(C)C	2892.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Pipecoloxylidide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9410000000-43bd727dc22ffb8b28dc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Pipecoloxylidide GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9120000000-06e277773e9f544d2472	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Pipecoloxylidide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Pipecoloxylidide 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 - 2,6-Pipecoloxylidide 10V, Positive-QTOF	splash10-0089-3890000000-e6a41960aa4ff4f1f47f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Pipecoloxylidide 20V, Positive-QTOF	splash10-00e9-5900000000-acacd980f8204606c127	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Pipecoloxylidide 40V, Positive-QTOF	splash10-05al-9200000000-bd44fb3e4bd915b5ac3d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Pipecoloxylidide 10V, Negative-QTOF	splash10-001i-0190000000-190a196fabb7087922c3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Pipecoloxylidide 20V, Negative-QTOF	splash10-01x0-0970000000-d817d8a22eba173349ef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Pipecoloxylidide 40V, Negative-QTOF	splash10-00xr-4900000000-d5d9b16c3fc961084418	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115282

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for 2,6-Pipecoloxylidide (HMDB0060725)

MOL for HMDB0060725 (2,6-Pipecoloxylidide)

3D MOL for HMDB0060725 (2,6-Pipecoloxylidide)

3D SDF for HMDB0060725 (2,6-Pipecoloxylidide)

3D-SDF for HMDB0060725 (2,6-Pipecoloxylidide)

PDB for HMDB0060725 (2,6-Pipecoloxylidide)

3D PDB for HMDB0060725 (2,6-Pipecoloxylidide)

SMILES for HMDB0060725 (2,6-Pipecoloxylidide)

INCHI for HMDB0060725 (2,6-Pipecoloxylidide)

Structure for HMDB0060725 (2,6-Pipecoloxylidide)

3D Structure for HMDB0060725 (2,6-Pipecoloxylidide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra