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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:40:31 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254396

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Meclofenoxate

Description

Meclofenoxate, also known as meclofenoxic acid, belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. Meclofenoxate is a very strong basic compound (based on its pKa). Meclofenoxate, as well as DMAE, have been found to increase the lifespans of mice by 30–50%. It is sold in Japan and some European countries, such as Germany, Hungary, and Austria, as a prescription drug. It is an ester of dimethylethanolamine (DMAE) and 4-chlorophenoxyacetic acid (pCPA). Meclofenoxate is considered to be very safe and high in tolerability. However, possible side effects may include, rarely, insomnia, dizziness, restlessness, muscle tremor, depression, nausea, muscle tension, and headache; these side effects may be due to overdosage and may indicate the need for the dosage to be reduced. In addition to Lucidril, meclofenoxate has also been marketed under the brand names Amipolen, Analux, Brenal, Cellative, Centrophenoxin, Cerebron, Cerutil, Closete, Helfergin, Lucidryl, Lutiaron, Marucotol, Proserout, Proseryl, and Ropoxyl. In elderly patients, meclofenoxate has been found clinically to improve memory, have a mentally stimulating effect, and improve general cognition. Meclofenoxate also increases cellular membrane phospholipids. This compound has been identified in human blood as reported by (PMID: 31557052 ). Meclofenoxate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Meclofenoxate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254396
     RDKit          3D
meclofenoxate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.2608    1.0060    0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.0250    0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -1.2543    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.1407   -1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6348   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -0.3421   -1.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2855   -0.4109   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.8038    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.0522   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -0.2331    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.0403    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7081   -0.1284    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0460    0.1369    2.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    0.5924    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5378    0.9401    1.2149 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2449    0.7650   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    0.4901   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837    0.8217    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126    2.0267    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315    0.8457    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652   -1.0718    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.0756    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489   -1.4111    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    1.2332   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920   -0.0088   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.7417   -1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244   -0.3797   -3.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    0.9695   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -0.7354   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.4787    2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4943   -0.0073    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.1137   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202    0.6226   -1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

  Mrv1652306031607142D          

 17 17  0  0  0  0            999 V2000
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  8  1  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254396

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16ClNO3/c1-14(2)7-8-16-12(15)9-17-11-5-3-10(13)4-6-11/h3-6H,7-9H2,1-2H3

> <INCHI_KEY>
XZTYGFHCIAKPGJ-UHFFFAOYSA-N

> <FORMULA>
C12H16ClNO3

> <MOLECULAR_WEIGHT>
257.71

> <EXACT_MASS>
257.0818711

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.867182049195197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(dimethylamino)ethyl 2-(4-chlorophenoxy)acetate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.0621411133333334

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.418003627339894

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
66.19880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(dimethylamino)ethyl 4-chlorophenoxyacetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254396
     RDKit          3D
meclofenoxate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.2608    1.0060    0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.0250    0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -1.2543    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.1407   -1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6348   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -0.3421   -1.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2855   -0.4109   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.8038    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.0522   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -0.2331    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.0403    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7081   -0.1284    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0460    0.1369    2.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    0.5924    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5378    0.9401    1.2149 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2449    0.7650   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    0.4901   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837    0.8217    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126    2.0267    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315    0.8457    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652   -1.0718    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.0756    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489   -1.4111    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    1.2332   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920   -0.0088   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.7417   -1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244   -0.3797   -3.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    0.9695   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -0.7354   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.4787    2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4943   -0.0073    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.1137   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202    0.6226   -1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0      12.003  -0.770   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   14                                                       
CONECT    8    7   16                                                       
CONECT    9   12   17                                                       
CONECT   10    3    4   13                                                  
CONECT   11    5    6   17                                                  
CONECT   12    9   15   16                                                  
CONECT   13   10                                                            
CONECT   14    1    2    7                                                  
CONECT   15   12                                                            
CONECT   16    8   12                                                       
CONECT   17    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0254396
HETATM    1  C1  UNL     1      -4.261   1.006   0.836  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.281   0.025   0.291  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.830  -1.254   0.768  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.416   0.141  -1.130  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.472  -0.635  -1.969  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.120  -0.342  -1.834  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.285  -0.411  -0.784  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.739  -0.804   0.317  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.163  -0.052  -0.817  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.760  -0.233   0.448  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.103   0.040   0.625  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.708  -0.128   1.853  1.00  0.00           C  
HETATM   13  C9  UNL     1       5.046   0.137   2.055  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.835   0.592   0.997  1.00  0.00           C  
HETATM   15 CL1  UNL     1       7.538   0.940   1.215  1.00  0.00          CL  
HETATM   16  C11 UNL     1       5.245   0.765  -0.232  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.900   0.490  -0.403  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.184   0.822   0.221  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.913   2.027   0.575  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.432   0.846   1.907  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.165  -1.072   1.807  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.121  -2.076   0.741  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.749  -1.411   0.158  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.245   1.233  -1.366  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.492  -0.009  -1.436  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.675  -1.742  -1.928  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.724  -0.380  -3.048  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.348   0.970  -1.145  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.610  -0.735  -1.597  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.134  -0.479   2.698  1.00  0.00           H  
HETATM   31  H14 UNL     1       5.494  -0.007   3.042  1.00  0.00           H  
HETATM   32  H15 UNL     1       5.800   1.114  -1.088  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.420   0.623  -1.374  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   28   29
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   16
CONECT   16   17   17   32
CONECT   17   33
END

HMDB0254396
     RDKit          3D
meclofenoxate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.2608    1.0060    0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.0250    0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -1.2543    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.1407   -1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6348   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -0.3421   -1.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2855   -0.4109   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.8038    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.0522   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -0.2331    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.0403    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7081   -0.1284    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0460    0.1369    2.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    0.5924    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5378    0.9401    1.2149 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2449    0.7650   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    0.4901   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837    0.8217    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126    2.0267    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315    0.8457    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652   -1.0718    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.0756    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489   -1.4111    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    1.2332   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920   -0.0088   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -1.7417   -1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244   -0.3797   -3.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    0.9695   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -0.7354   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.4787    2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4943   -0.0073    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.1137   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202    0.6226   -1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Meclofenoxic acid	Generator
Centrophenoxine	ChEMBL, MeSH
Meclofenoxate HCL	ChEMBL
Clophenoxate	ChEMBL
Meclofenoxic acid HCL	Generator
Clophenoxic acid	Generator
Atsefen	MeSH
Cetrexin	MeSH
Cerutil	MeSH
Alpharma brand OF meclofenoxate hydrochloride	MeSH
Helfergin	MeSH
Lundbeck brand OF meclofenoxate hydrochloride	MeSH
Meclofenoxate hydrochloride	MeSH
2-(Dimethylamino)ethyl 2-(4-chlorophenoxy)acetic acid	Generator

Chemical Formula

C₁₂H₁₆ClNO₃

Average Molecular Weight

257.71

Monoisotopic Molecular Weight

257.0818711

IUPAC Name

2-(dimethylamino)ethyl 2-(4-chlorophenoxy)acetate

Traditional Name

2-(dimethylamino)ethyl 4-chlorophenoxyacetate

CAS Registry Number

Not Available

SMILES

CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C12H16ClNO3/c1-14(2)7-8-16-12(15)9-17-11-5-3-10(13)4-6-11/h3-6H,7-9H2,1-2H3

InChI Key

XZTYGFHCIAKPGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:6712 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	2.4	ALOGPS
logP	2.06	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	152.875	30932474
DeepCCS	[M-H]-	150.517	30932474
DeepCCS	[M-2H]-	184.371	30932474
DeepCCS	[M+Na]+	159.247	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
meclofenoxate	CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1	2652.8	Standard polar	33892256
meclofenoxate	CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1	1836.7	Standard non polar	33892256
meclofenoxate	CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1	1862.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Meclofenoxate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-b651e6873e329880c714	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meclofenoxate 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 - Meclofenoxate 10V, Negative-QTOF	splash10-0ap0-3950000000-fea2e0edc2c2f6eb346b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 20V, Negative-QTOF	splash10-004i-1910000000-4803eb35c1395457afef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 40V, Negative-QTOF	splash10-004i-4900000000-923fe2ff431e0ef6fe1c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 10V, Negative-QTOF	splash10-0a70-1950000000-80ddbce4c78408ae9202	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 20V, Negative-QTOF	splash10-004i-2900000000-b7446a91668374cb14ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 40V, Negative-QTOF	splash10-0059-9800000000-87b182e9b83fb0ad849d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 10V, Positive-QTOF	splash10-0adi-6980000000-9112918bcdfaa6f6515c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 20V, Positive-QTOF	splash10-00fr-9720000000-b971c1b643a68cc573be	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 40V, Positive-QTOF	splash10-004i-9800000000-138a58e96f0e61f5ea1b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 10V, Positive-QTOF	splash10-0a4i-2190000000-b1632d794f3a9a49ef94	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 20V, Positive-QTOF	splash10-00di-9720000000-0cbfb3361ae90671ce2c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenoxate 40V, Positive-QTOF	splash10-0229-9500000000-44a783b6e592957c1389	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13758

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C08195

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meclofenoxate

METLIN ID

Not Available

PubChem Compound

4039

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Meclofenoxate (HMDB0254396)

MOL for HMDB0254396 (Meclofenoxate)

3D MOL for HMDB0254396 (Meclofenoxate)

3D SDF for HMDB0254396 (Meclofenoxate)

3D-SDF for HMDB0254396 (Meclofenoxate)

PDB for HMDB0254396 (Meclofenoxate)

3D PDB for HMDB0254396 (Meclofenoxate)

SMILES for HMDB0254396 (Meclofenoxate)

INCHI for HMDB0254396 (Meclofenoxate)

Structure for HMDB0254396 (Meclofenoxate)

3D Structure for HMDB0254396 (Meclofenoxate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra