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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:21 UTC

Update Date

2019-07-23 07:15:32 UTC

HMDB ID

HMDB0060991

Secondary Accession Numbers

HMDB60991

Metabolite Identification

Common Name

hydroxychlorpromazine

Description

hydroxychlorpromazine 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

HMDB0060991
     RDKit          3D
hydroxychlorpromazine
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.8517   -1.1693    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.6259    1.2177 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304    0.7126    1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -0.6150    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -0.1993    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681   -0.2023   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    0.1577   -0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.8536    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264   -2.1213    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.1349    0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -2.9348    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -3.9913    1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -1.7019    0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671   -0.7001    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995    0.8445    0.1264 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539    1.9257   -0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    3.2038   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    4.1134   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.6642   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    4.8108   -2.2267 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    2.3662   -1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4751    1.4687   -0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6857   -0.4465    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692   -1.4077   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -2.0956    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547    1.4587    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.6466    2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561    1.0976    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266    0.0119   -0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -1.6760   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.8548    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.7709    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    0.3934   -1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.2472   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -2.3399    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -4.0944    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091   -4.6658    1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801   -1.5414    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    3.5347   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    5.1267   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877    2.1430   -1.4910 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  1  0
  8  9  2  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
 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  7  1  0
 14  8  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  END


  Mrv0541 07091309112D          

 22 24  0  0  0  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    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    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    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
    2.1434    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16  7  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 12  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060991

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H19ClN2OS/c1-19(2)8-3-9-20-14-6-5-13(21)11-17(14)22-16-7-4-12(18)10-15(16)20/h4-7,10-11,21H,3,8-9H2,1-2H3

> <INCHI_KEY>
HICFFJZGXWEIHN-UHFFFAOYSA-N

> <FORMULA>
C17H19ClN2OS

> <MOLECULAR_WEIGHT>
334.864

> <EXACT_MASS>
334.090661637

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.524227525873904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-chloro-10-[3-(dimethylamino)propyl]-10H-phenothiazin-3-ol

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
3.9215394387845053

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.159284887309672

> <JCHEM_PKA_STRONGEST_BASIC>
9.146738656358346

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
95.73719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxychlorpromazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060991
     RDKit          3D
hydroxychlorpromazine
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.8517   -1.1693    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.6259    1.2177 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304    0.7126    1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -0.6150    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -0.1993    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681   -0.2023   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    0.1577   -0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.8536    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264   -2.1213    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.1349    0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -2.9348    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -3.9913    1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -1.7019    0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671   -0.7001    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995    0.8445    0.1264 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539    1.9257   -0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    3.2038   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    4.1134   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.6642   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    4.8108   -2.2267 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    2.3662   -1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4751    1.4687   -0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6857   -0.4465    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692   -1.4077   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -2.0956    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547    1.4587    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.6466    2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561    1.0976    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266    0.0119   -0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -1.6760   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.8548    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.7709    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    0.3934   -1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.2472   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -2.3399    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -4.0944    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091   -4.6658    1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801   -1.5414    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    3.5347   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    5.1267   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877    2.1430   -1.4910 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  1  0
  8  9  2  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
 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  7  1  0
 14  8  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -1.334  10.010   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0      -4.001   5.390   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       4.001   6.930   0.000  0.00  0.00           S+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3    8    9                                                       
CONECT    4    7   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7    4   16                                                       
CONECT    8    3   19                                                       
CONECT    9    3   20                                                       
CONECT   10   12   15                                                       
CONECT   11   13   17                                                       
CONECT   12    4   10   18                                                  
CONECT   13    5   11   21                                                  
CONECT   14    6   17   20                                                  
CONECT   15   10   16   20                                                  
CONECT   16    7   15   22                                                  
CONECT   17   11   14   22                                                  
CONECT   18   12                                                            
CONECT   19    1    2    8                                                  
CONECT   20    9   14   15                                                  
CONECT   21   13                                                            
CONECT   22   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060991
HETATM    1  C1  UNL     1       4.852  -1.169   0.682  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.588  -0.626   1.218  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.930   0.713   1.688  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.668  -0.615   0.132  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.257  -0.199   0.483  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.368  -0.202  -0.725  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.008   0.158  -0.467  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.835  -0.854   0.102  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.326  -2.121   0.382  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.082  -3.135   0.940  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.396  -2.935   1.250  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.108  -3.991   1.810  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.926  -1.702   0.986  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.167  -0.700   0.431  1.00  0.00           C  
HETATM   15  S1  UNL     1      -3.999   0.844   0.126  1.00  0.00           S  
HETATM   16  C12 UNL     1      -2.754   1.926  -0.551  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.166   3.204  -0.825  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.262   4.113  -1.348  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.979   3.664  -1.563  1.00  0.00           C  
HETATM   20 CL1  UNL     1       0.189   4.811  -2.227  1.00  0.00          CL  
HETATM   21  C16 UNL     1      -0.568   2.366  -1.283  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.475   1.469  -0.763  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.686  -0.446   0.775  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.769  -1.408  -0.397  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.136  -2.096   1.222  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.155   1.459   1.521  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.235   0.647   2.760  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.856   1.098   1.161  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.027   0.012  -0.732  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.593  -1.676  -0.246  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.356   0.855   0.902  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.851  -0.771   1.327  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.863   0.393  -1.516  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.447  -1.247  -1.173  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.302  -2.340   0.153  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.602  -4.094   1.125  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.609  -4.666   1.255  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.980  -1.541   1.234  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.196   3.535  -0.642  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.573   5.127  -1.570  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.488   2.143  -1.491  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   22
CONECT    8    9    9   14
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   13
CONECT   12   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

HMDB0060991
     RDKit          3D
hydroxychlorpromazine
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.8517   -1.1693    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.6259    1.2177 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304    0.7126    1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -0.6150    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -0.1993    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681   -0.2023   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    0.1577   -0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.8536    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264   -2.1213    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.1349    0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -2.9348    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -3.9913    1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -1.7019    0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671   -0.7001    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995    0.8445    0.1264 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539    1.9257   -0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    3.2038   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    4.1134   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.6642   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    4.8108   -2.2267 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    2.3662   -1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4751    1.4687   -0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6857   -0.4465    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692   -1.4077   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -2.0956    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547    1.4587    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.6466    2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561    1.0976    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266    0.0119   -0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -1.6760   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.8548    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.7709    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    0.3934   -1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.2472   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -2.3399    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -4.0944    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091   -4.6658    1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801   -1.5414    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    3.5347   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    5.1267   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877    2.1430   -1.4910 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  1  0
  8  9  2  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
 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  7  1  0
 14  8  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxychlorpromazine monohydrochloride	HMDB

Chemical Formula

C₁₇H₁₉ClN₂OS

Average Molecular Weight

334.864

Monoisotopic Molecular Weight

334.090661637

IUPAC Name

8-chloro-10-[3-(dimethylamino)propyl]-10H-phenothiazin-3-ol

Traditional Name

7-hydroxychlorpromazine

CAS Registry Number

Not Available

SMILES

CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=C(O)C=C2

InChI Identifier

InChI=1S/C17H19ClN2OS/c1-19(2)8-3-9-20-14-6-5-13(21)11-17(14)22-16-7-4-12(18)10-15(16)20/h4-7,10-11,21H,3,8-9H2,1-2H3

InChI Key

HICFFJZGXWEIHN-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
1-hydroxy-2-unsubstituted benzenoid
Para-thiazine
Aryl chloride
Aryl halide
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060991)
Liver (HMDB: HMDB0060991)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060991)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060991)

Cellular substructure

Cytoplasm (HMDB: HMDB0060991)
Membrane (HMDB: HMDB0060991)

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	0.022 g/L	ALOGPS
logP	4.68	ALOGPS
logP	3.92	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.16	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.74 m³·mol⁻¹	ChemAxon
Polarizability	36.52 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]+	174.921	30932474
DeepCCS	[M-H]-	172.563	30932474
DeepCCS	[M-2H]-	205.449	30932474
DeepCCS	[M+Na]+	181.014	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	172.7	32859911
AllCCS	[M+HCOO]-	172.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
hydroxychlorpromazine	CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=C(O)C=C2	3824.2	Standard polar	33892256
hydroxychlorpromazine	CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=C(O)C=C2	2721.1	Standard non polar	33892256
hydroxychlorpromazine	CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=C(O)C=C2	2852.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
hydroxychlorpromazine,1TMS,isomer #1	CN(C)CCCN1C2=CC=C(O[Si](C)(C)C)C=C2SC2=CC=C(Cl)C=C21	2819.8	Semi standard non polar	33892256
hydroxychlorpromazine,1TBDMS,isomer #1	CN(C)CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2SC2=CC=C(Cl)C=C21	3029.0	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 - hydroxychlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-9171000000-fa2621ccd32e1faca6d5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxychlorpromazine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9126000000-516111bdc31d78576e5a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxychlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxychlorpromazine 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 - hydroxychlorpromazine 10V, Positive-QTOF	splash10-000i-1019000000-f78d7fb1aaa159975d9e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 20V, Positive-QTOF	splash10-000l-9076000000-9ac5f74b924d09b3f95d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 40V, Positive-QTOF	splash10-01bl-9040000000-b18c38578c8ed0f34e5a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 10V, Negative-QTOF	splash10-001i-0019000000-9bc6b82bfff9f78d43fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 20V, Negative-QTOF	splash10-0541-0395000000-68832eb5a3bb1b43329f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 40V, Negative-QTOF	splash10-01ot-3190000000-28eed02a43ecf48846b1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 10V, Positive-QTOF	splash10-000i-0009000000-d483d59a3c2925aeb4a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 20V, Positive-QTOF	splash10-000i-9003000000-2bfea0a1e622331fd223	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 40V, Positive-QTOF	splash10-052r-9000000000-899499bafdd3463586b4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 10V, Negative-QTOF	splash10-001i-0009000000-32bc2e04936d8ee0d295	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 20V, Negative-QTOF	splash10-001i-0049000000-d566d956c3fc106cacde	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxychlorpromazine 40V, Negative-QTOF	splash10-001j-4090000000-45764c16ba80514742eb	2021-09-25	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16414

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 hydroxychlorpromazine (HMDB0060991)

MOL for HMDB0060991 (hydroxychlorpromazine)

3D MOL for HMDB0060991 (hydroxychlorpromazine)

3D SDF for HMDB0060991 (hydroxychlorpromazine)

3D-SDF for HMDB0060991 (hydroxychlorpromazine)

PDB for HMDB0060991 (hydroxychlorpromazine)

3D PDB for HMDB0060991 (hydroxychlorpromazine)

SMILES for HMDB0060991 (hydroxychlorpromazine)

INCHI for HMDB0060991 (hydroxychlorpromazine)

Structure for HMDB0060991 (hydroxychlorpromazine)

3D Structure for HMDB0060991 (hydroxychlorpromazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra