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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:42:30 UTC

Update Date

2019-07-23 07:14:47 UTC

HMDB ID

HMDB0060655

Secondary Accession Numbers

HMDB60655

Metabolite Identification

Common Name

3-Hydroxylidocaine

Description

3-Hydroxylidocaine belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 3-Hydroxylidocaine is a metabolite of lidocaine. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery. 3-Hydroxylidocaine is a very strong basic compound (based on its pKa). 3-hydroxylidocaine can be biosynthesized from lidocaine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 3A4. In humans, 3-hydroxylidocaine is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.

Structure

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

HMDB0060655
     RDKit          3D
3-Hydroxylidocaine
 40 40  0  0  0  0  0  0  0  0999 V2000
    3.7325   -0.2819   -2.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -0.8001   -1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.0177   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949   -0.3640    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.4805    1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -0.2990    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.1316   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.7099   -1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439   -0.1320    0.8232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    0.2195    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.4375    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030    2.4344    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    1.7311    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8465    0.8078   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045   -0.4323   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1163   -1.3468   -1.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.6837   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -1.9928   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -1.0611   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.0771   -3.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.6561   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -1.8947   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357   -0.6484   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8035   -1.4451    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7926   -0.2858   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000    0.0418    2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0395    0.7144    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.4605    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    0.3121    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.3522    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6151    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    3.3523    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033    2.7925    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057    2.0839    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    2.6771    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661    1.0194   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -2.2403   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -2.0834   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -2.8166    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -2.1926   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

 
  Mrv0541 06181310422D          
 
 18 18  0  0  0  0            999 V2000
   13.9621  -11.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6783  -11.9809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2491  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9621  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3913  -11.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5362  -11.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2525  -12.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2491  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6715  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1042  -11.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3845  -10.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5362  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8206  -11.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5369  -11.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8206  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2430  -11.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5369  -10.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2492   -9.4876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060655

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H22N2O2/c1-5-16(6-2)9-13(18)15-14-10(3)7-8-12(17)11(14)4/h7-8,17H,5-6,9H2,1-4H3,(H,15,18)

> <INCHI_KEY>
PMGUCIDDSCRAMY-UHFFFAOYSA-N

> <FORMULA>
C14H22N2O2

> <MOLECULAR_WEIGHT>
250.3367

> <EXACT_MASS>
250.168127958

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.693168240173527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
2.539348037999999

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.92885480147072

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.03988825004344

> <JCHEM_PKA_STRONGEST_BASIC>
7.732556152210769

> <JCHEM_POLAR_SURFACE_AREA>
52.57000000000001

> <JCHEM_REFRACTIVITY>
75.9105

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060655
     RDKit          3D
3-Hydroxylidocaine
 40 40  0  0  0  0  0  0  0  0999 V2000
    3.7325   -0.2819   -2.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -0.8001   -1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.0177   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949   -0.3640    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.4805    1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -0.2990    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.1316   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.7099   -1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439   -0.1320    0.8232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    0.2195    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.4375    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030    2.4344    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    1.7311    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8465    0.8078   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045   -0.4323   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1163   -1.3468   -1.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.6837   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -1.9928   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -1.0611   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.0771   -3.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.6561   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -1.8947   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357   -0.6484   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8035   -1.4451    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7926   -0.2858   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000    0.0418    2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0395    0.7144    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.4605    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    0.3121    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.3522    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6151    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    3.3523    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033    2.7925    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057    2.0839    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    2.6771    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661    1.0194   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -2.2403   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -2.0834   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -2.8166    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -2.1926   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      26.063 -21.591   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      27.399 -22.364   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      24.732 -22.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.063 -20.051   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.730 -21.585   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.401 -21.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.738 -23.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.732 -19.284   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.387 -19.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.061 -22.364   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      28.718 -20.039   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      23.401 -20.051   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      31.398 -21.585   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      32.736 -22.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.398 -20.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.054 -21.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.736 -19.278   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      24.732 -17.710   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3   12                                                       
CONECT    7    3                                                            
CONECT    8    4   12   18                                                  
CONECT    9    4                                                            
CONECT   10    5   13                                                       
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14                                                            
CONECT   17   15                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0060655
HETATM    1  C1  UNL     1       3.733  -0.282  -2.599  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.596  -0.800  -1.705  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.662  -0.018  -0.481  1.00  0.00           N  
HETATM    4  C3  UNL     1       3.895  -0.364   0.253  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.958   0.481   1.484  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.591  -0.299   0.416  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.251   0.132  -0.033  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.123   0.710  -1.145  1.00  0.00           O  
HETATM    9  N2  UNL     1      -0.844  -0.132   0.823  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.183   0.220   0.522  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.750   1.438   0.848  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.903   2.434   1.545  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.063   1.731   0.538  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.847   0.808  -0.111  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.305  -0.432  -0.456  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.116  -1.347  -1.109  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.978  -0.684  -0.123  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.431  -1.993  -0.493  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.542  -1.061  -2.590  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.369  -0.077  -3.625  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.168   0.656  -2.208  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.729  -1.895  -1.524  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.636  -0.648  -2.213  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.804  -1.445   0.574  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.793  -0.286  -0.357  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.500   0.042   2.374  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.040   0.714   1.670  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.472   1.461   1.296  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.795   0.312   1.348  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.594  -1.352   0.777  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.653  -0.615   1.732  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.515   3.352   1.776  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.103   2.793   0.844  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.506   2.084   2.507  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.498   2.677   0.794  1.00  0.00           H  
HETATM   36  H18 UNL     1      -5.866   1.019  -0.359  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.722  -2.240  -1.354  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.341  -2.083  -0.412  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.931  -2.817   0.095  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.695  -2.193  -1.552  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    6
CONECT    4    5   24   25
CONECT    5   26   27   28
CONECT    6    7   29   30
CONECT    7    8    8    9
CONECT    9   10   31
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   32   33   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   17   17
CONECT   16   37
CONECT   17   18
CONECT   18   38   39   40
END

HMDB0060655
     RDKit          3D
3-Hydroxylidocaine
 40 40  0  0  0  0  0  0  0  0999 V2000
    3.7325   -0.2819   -2.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -0.8001   -1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.0177   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949   -0.3640    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.4805    1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -0.2990    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.1316   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.7099   -1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439   -0.1320    0.8232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    0.2195    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.4375    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030    2.4344    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    1.7311    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8465    0.8078   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045   -0.4323   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1163   -1.3468   -1.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.6837   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -1.9928   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421   -1.0611   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.0771   -3.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.6561   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -1.8947   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357   -0.6484   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8035   -1.4451    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7926   -0.2858   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000    0.0418    2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0395    0.7144    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.4605    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    0.3121    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.3522    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -0.6151    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    3.3523    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033    2.7925    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057    2.0839    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    2.6771    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661    1.0194   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -2.2403   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -2.0834   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -2.8166    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -2.1926   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₂₂N₂O₂

Average Molecular Weight

250.3367

Monoisotopic Molecular Weight

250.168127958

IUPAC Name

2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

Traditional Name

2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H22N2O2/c1-5-16(6-2)9-13(18)15-14-10(3)7-8-12(17)11(14)4/h7-8,17H,5-6,9H2,1-4H3,(H,15,18)

InChI Key

PMGUCIDDSCRAMY-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
Xylenol
Anilide
O-cresol
P-cresol
M-xylene
Xylene
N-arylamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amino acid amide (CHEBI:80567 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060655)

Organ

Liver (HMDB: HMDB0060655)
Kidney (HMDB: HMDB0060655)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060655)

Cellular substructure

Cytoplasm (HMDB: HMDB0060655)
Membrane (HMDB: HMDB0060655)

Source

Endogenous

Endogenous (HMDB: HMDB0060655)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lidocaine (Antiarrhythmic) Action Pathway (PathBank: SMP0000328)
Lidocaine (Local Anaesthetic) Action Pathway (PathBank: SMP0000398)

Metabolic pathway

Lidocaine (Local Anaesthetic) Metabolism Pathway (PathBank: SMP0000620)

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	1.3 g/L	ALOGPS
logP	1.69	ALOGPS
logP	2.54	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.04	ChemAxon
pKa (Strongest Basic)	7.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.91 m³·mol⁻¹	ChemAxon
Polarizability	28.69 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]+	160.861	31661259
DarkChem	[M-H]-	158.973	31661259
DeepCCS	[M+H]+	163.122	30932474
DeepCCS	[M-H]-	160.764	30932474
DeepCCS	[M-2H]-	193.65	30932474
DeepCCS	[M+Na]+	169.215	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.6	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxylidocaine	CCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C	2923.2	Standard polar	33892256
3-Hydroxylidocaine	CCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C	2126.2	Standard non polar	33892256
3-Hydroxylidocaine	CCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C	2172.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxylidocaine,1TMS,isomer #1	CCN(CC)CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C	2157.7	Semi standard non polar	33892256
3-Hydroxylidocaine,1TMS,isomer #2	CCN(CC)CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C	1947.4	Semi standard non polar	33892256
3-Hydroxylidocaine,2TMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	1988.2	Semi standard non polar	33892256
3-Hydroxylidocaine,2TMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2057.7	Standard non polar	33892256
3-Hydroxylidocaine,2TMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C	2335.1	Standard polar	33892256
3-Hydroxylidocaine,1TBDMS,isomer #1	CCN(CC)CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C	2426.0	Semi standard non polar	33892256
3-Hydroxylidocaine,1TBDMS,isomer #2	CCN(CC)CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C	2214.5	Semi standard non polar	33892256
3-Hydroxylidocaine,2TBDMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2496.1	Semi standard non polar	33892256
3-Hydroxylidocaine,2TBDMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2446.3	Standard non polar	33892256
3-Hydroxylidocaine,2TBDMS,isomer #1	CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C	2593.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9610000000-7d9e7465a3e0b86f4e10	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4r-9241000000-6c2fc67a46d746d33c94	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxylidocaine 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 - 3-Hydroxylidocaine 20V, Positive-QTOF	splash10-000i-9000000000-4041439bd0fd4cf8d790	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOF	splash10-0f79-9050000000-fd33f5e9645eebea97b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOF	splash10-0udr-7090000000-e12b82694dc9a32cacc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOF	splash10-000i-9000000000-ed4771fea10716df5db5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOF	splash10-0udr-7090000000-8c5bac2e6e0519905c1b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 0V, Positive-QTOF	splash10-0udi-0090000000-8570de4f92c182169499	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOF	splash10-000i-9000000000-bd37225fee133191cf61	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 0V, Positive-QTOF	splash10-0udi-0090000000-ed309985d4bd9c39233e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Negative-QTOF	splash10-053i-2900000000-6477f8d10de3ae00fc3e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Negative-QTOF	splash10-000i-0900000000-77e96289ee434fe70d61	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOF	splash10-0002-0290000000-0c7cb9ce98125c219def	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOF	splash10-000i-0920000000-0852a8bcf3d408b828c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOF	splash10-000i-9000000000-7560cc1a08f730a340c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOF	splash10-000i-9000000000-1496edf216edbb2a3e79	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOF	splash10-000i-9010000000-ad5e26b784dac6c93a4c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Positive-QTOF	splash10-000i-9000000000-02759b67c995186ef23a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOF	splash10-0a4r-9000000000-da6bc9e6cf9a4198ce99	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOF	splash10-0002-0190000000-cdc94b355bef03bf4465	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOF	splash10-0072-2980000000-acaf3c5aea41c1d8ec7f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Negative-QTOF	splash10-059f-9800000000-ad581d0e4a1f21078689	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOF	splash10-0udi-1090000000-7dce5a6948f756fcfd54	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Positive-QTOF	splash10-000i-9610000000-16e94f02639a739b0e39	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOF	splash10-0a4r-9300000000-cc8630abd8a5e02e9897	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOF	splash10-000j-0980000000-b9615244ae6ddc09718f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOF	splash10-000i-2900000000-16a846300720890f7063	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Lidocaine (Local Anaesthetic) Action Pathway		Not Available
Lidocaine (Local Anaesthetic) Metabolism Pathway		Not Available
Lidocaine (Antiarrhythmic) 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	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

C16560

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161824

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 3-Hydroxylidocaine (HMDB0060655)

MOL for HMDB0060655 (3-Hydroxylidocaine)

3D MOL for HMDB0060655 (3-Hydroxylidocaine)

3D SDF for HMDB0060655 (3-Hydroxylidocaine)

3D-SDF for HMDB0060655 (3-Hydroxylidocaine)

PDB for HMDB0060655 (3-Hydroxylidocaine)

3D PDB for HMDB0060655 (3-Hydroxylidocaine)

SMILES for HMDB0060655 (3-Hydroxylidocaine)

INCHI for HMDB0060655 (3-Hydroxylidocaine)

Structure for HMDB0060655 (3-Hydroxylidocaine)

3D Structure for HMDB0060655 (3-Hydroxylidocaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra