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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 16:58:09 UTC

Update Date

2019-07-23 07:14:37 UTC

HMDB ID

HMDB0060573

Secondary Accession Numbers

HMDB60573

Metabolite Identification

Common Name

Chlorpromazine-N-oxide

Description

Chlorpromazine-N-oxide is a metabolite of chlorpromazine. Chlorpromazine (as chlorpromazine hydrochloride, abbreviated CPZ; marketed in the United States as Thorazine and elsewhere as Largactil) is a typical antipsychotic. First synthesized on December 11, 1950, chlorpromazine was the first drug developed with specific antipsychotic action, and would serve as the prototype for the phenothiazine class of drugs, which later grew to comprise several other agents. (Wikipedia)

Structure

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

HMDB0060573
     RDKit          3D
Chlorpromazine-N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.2610   -1.3595    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020   -0.2067   -0.6164 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5773    0.2549   -0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -0.5742   -1.8144 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.5524    0.9395   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.7218    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    0.2315   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.0389   -0.0949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1022    0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886   -2.0647    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -3.1851    1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -3.4049    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239   -2.4738    1.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -1.3793    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -0.2473    0.8397 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3566    1.0672   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    2.0781   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742    3.1596   -1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    3.1840   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    4.5511   -2.5354 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086    2.1671   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    1.0697   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775   -1.1570    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -2.2424   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152   -1.6701    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    0.7879   -0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205   -0.5869   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4430    1.0050   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    1.7023   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    1.4136    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    1.7193    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    0.0809    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6413   -0.8303   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.8246   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -1.9802    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0085   -3.9127    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3233   -4.2693    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0344   -2.6632    2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    2.0613   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    3.9579   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    2.2934   -1.5400 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  CHG  2   2   1   4  -1
M  END


  Mrv0541 06151309582D          

 22 24  0  0  0  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    2.1434   -1.2375    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 11  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  6  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 19 10  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20 11  1  0  0  0  0
 21 20  2  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060573

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H19ClN2OS/c1-20(2,21)11-5-10-19-14-6-3-4-7-16(14)22-17-9-8-13(18)12-15(17)19/h3-4,6-9,12H,5,10-11H2,1-2H3

> <INCHI_KEY>
LFDFWIIFGRXCFR-UHFFFAOYSA-N

> <FORMULA>
C17H19ClN2OS

> <MOLECULAR_WEIGHT>
334.864

> <EXACT_MASS>
334.090661637

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.10459648198918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropanamine oxide

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
3.4106250590000005

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.1242209024963445

> <JCHEM_POLAR_SURFACE_AREA>
30.12

> <JCHEM_REFRACTIVITY>
95.80119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorpromazine n-oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060573
     RDKit          3D
Chlorpromazine-N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.2610   -1.3595    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020   -0.2067   -0.6164 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5773    0.2549   -0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -0.5742   -1.8144 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.5524    0.9395   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.7218    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    0.2315   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.0389   -0.0949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1022    0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886   -2.0647    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -3.1851    1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -3.4049    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239   -2.4738    1.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -1.3793    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -0.2473    0.8397 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3566    1.0672   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    2.0781   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742    3.1596   -1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    3.1840   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    4.5511   -2.5354 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086    2.1671   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    1.0697   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775   -1.1570    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -2.2424   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152   -1.6701    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    0.7879   -0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205   -0.5869   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4430    1.0050   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    1.7023   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    1.4136    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    1.7193    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    0.0809    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6413   -0.8303   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.8246   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -1.9802    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0085   -3.9127    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3233   -4.2693    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0344   -2.6632    2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    2.0613   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    3.9579   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    2.2934   -1.5400 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.437  -4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       0.000   1.540   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       1.897  -1.746   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       5.335   4.620   0.000  0.00  0.00           S+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5   10   11                                                       
CONECT    6    3   14                                                       
CONECT    7    4   16                                                       
CONECT    8    9   13                                                       
CONECT    9    8   17                                                       
CONECT   10    5   19                                                       
CONECT   11    5   20                                                       
CONECT   12   13   15                                                       
CONECT   13    8   12   18                                                  
CONECT   14    6   16   19                                                  
CONECT   15   12   17   19                                                  
CONECT   16    7   14   22                                                  
CONECT   17    9   15   22                                                  
CONECT   18   13                                                            
CONECT   19   10   14   15                                                  
CONECT   20    1    2   11   21                                             
CONECT   21   20                                                            
CONECT   22   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060573
HETATM    1  C1  UNL     1       3.261  -1.359   0.231  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.202  -0.207  -0.616  1.00  0.00           N1+
HETATM    3  C2  UNL     1       4.577   0.255  -0.928  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.657  -0.574  -1.814  1.00  0.00           O1-
HETATM    5  C3  UNL     1       2.552   0.940  -0.045  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.191   0.722   0.532  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.264   0.231  -0.553  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.109   0.039  -0.095  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.446  -1.102   0.681  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.489  -2.065   1.004  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.780  -3.185   1.756  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.060  -3.405   2.230  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.024  -2.474   1.928  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.703  -1.379   1.183  1.00  0.00           C  
HETATM   15  S1  UNL     1      -4.032  -0.247   0.840  1.00  0.00           S  
HETATM   16  C12 UNL     1      -3.357   1.067  -0.116  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.191   2.078  -0.483  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.774   3.160  -1.221  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.465   3.184  -1.581  1.00  0.00           C  
HETATM   20 CL1  UNL     1      -1.859   4.551  -2.535  1.00  0.00          CL  
HETATM   21  C16 UNL     1      -1.609   2.167  -1.217  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.029   1.070  -0.469  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.877  -1.157   1.259  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.735  -2.242  -0.219  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.315  -1.670   0.338  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.902   0.788  -0.009  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.221  -0.587  -1.199  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.443   1.005  -1.734  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.507   1.702  -0.884  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.245   1.414   0.696  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.848   1.719   0.926  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.223   0.081   1.419  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.641  -0.830  -0.782  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.382   0.825  -1.448  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.523  -1.980   0.675  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.009  -3.913   1.987  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.323  -4.269   2.821  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.034  -2.663   2.312  1.00  0.00           H  
HETATM   39  H17 UNL     1      -5.239   2.061  -0.196  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.435   3.958  -1.511  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.600   2.293  -1.540  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   21
CONECT   21   22   22   41
END

HMDB0060573
     RDKit          3D
Chlorpromazine-N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.2610   -1.3595    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020   -0.2067   -0.6164 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5773    0.2549   -0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -0.5742   -1.8144 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.5524    0.9395   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.7218    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    0.2315   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.0389   -0.0949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1022    0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886   -2.0647    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -3.1851    1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -3.4049    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239   -2.4738    1.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -1.3793    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -0.2473    0.8397 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3566    1.0672   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    2.0781   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742    3.1596   -1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    3.1840   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    4.5511   -2.5354 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086    2.1671   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    1.0697   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775   -1.1570    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -2.2424   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152   -1.6701    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    0.7879   -0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205   -0.5869   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4430    1.0050   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    1.7023   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    1.4136    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    1.7193    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    0.0809    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6413   -0.8303   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.8246   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -1.9802    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0085   -3.9127    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3233   -4.2693    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0344   -2.6632    2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    2.0613   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    3.9579   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    2.2934   -1.5400 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Chloro-10-(3'-dimethyloxidoaminopropyl)phenothiazine	ChEBI

Chemical Formula

C₁₇H₁₉ClN₂OS

Average Molecular Weight

334.864

Monoisotopic Molecular Weight

334.090661637

IUPAC Name

3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropanamine oxide

Traditional Name

chlorpromazine n-oxide

CAS Registry Number

Not Available

SMILES

CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C17H19ClN2OS/c1-20(2,21)11-5-10-19-14-6-3-4-7-16(14)22-17-9-8-13(18)12-15(17)19/h3-4,6-9,12H,5,10-11H2,1-2H3

InChI Key

LFDFWIIFGRXCFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Aryl chloride
Aryl halide
Benzenoid
Trialkyl amine oxide
Tertiary amine
N-oxide
Azacycle
Trisubstituted n-oxide
Thioether
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:3648 )
organochlorine compound (CHEBI:3648 )
N-oxide (CHEBI:3648 )

Ontology

Not Available

Kidney (HMDB: HMDB0060573)
Liver (HMDB: HMDB0060573)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060573)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060573)

Cellular substructure

Cytoplasm (HMDB: HMDB0060573)
Membrane (HMDB: HMDB0060573)

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	0.00058 g/L	ALOGPS
logP	1.84	ALOGPS
logP	3.41	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	4.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.8 m³·mol⁻¹	ChemAxon
Polarizability	36.1 Å³	ChemAxon
Number of Rings	3	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]+	166.783	30932474
DeepCCS	[M-H]-	164.425	30932474
DeepCCS	[M-2H]-	197.311	30932474
DeepCCS	[M+Na]+	172.876	30932474
AllCCS	[M+H]+	174.1	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	179.1	32859911
AllCCS	[M+HCOO]-	179.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorpromazine-N-oxide	CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	3726.5	Standard polar	33892256
Chlorpromazine-N-oxide	CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2229.5	Standard non polar	33892256
Chlorpromazine-N-oxide	CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2620.6	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 - Chlorpromazine-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3192000000-b58a61a04eff14215133	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpromazine-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpromazine-N-oxide 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 - Chlorpromazine-N-oxide 10V, Negative-QTOF	splash10-001i-0009000000-bb74226afd9b458ad76c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine-N-oxide 20V, Negative-QTOF	splash10-001i-1069000000-47ec271b54f6c21c513e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine-N-oxide 40V, Negative-QTOF	splash10-001i-0190000000-ef93452eac6268285bd9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine-N-oxide 10V, Positive-QTOF	splash10-000i-0139000000-30e61f6508e6c1c508ec	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine-N-oxide 20V, Positive-QTOF	splash10-0fe0-2598000000-5c9185020bd700a12cb2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine-N-oxide 40V, Positive-QTOF	splash10-0f7x-9350000000-f6eecad2761081125fe3	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

C10966

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443037

PDB ID

Not Available

ChEBI ID

3648

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 Chlorpromazine-N-oxide (HMDB0060573)

MOL for HMDB0060573 (Chlorpromazine-N-oxide)

3D MOL for HMDB0060573 (Chlorpromazine-N-oxide)

3D SDF for HMDB0060573 (Chlorpromazine-N-oxide)

3D-SDF for HMDB0060573 (Chlorpromazine-N-oxide)

PDB for HMDB0060573 (Chlorpromazine-N-oxide)

3D PDB for HMDB0060573 (Chlorpromazine-N-oxide)

SMILES for HMDB0060573 (Chlorpromazine-N-oxide)

INCHI for HMDB0060573 (Chlorpromazine-N-oxide)

Structure for HMDB0060573 (Chlorpromazine-N-oxide)

3D Structure for HMDB0060573 (Chlorpromazine-N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra