Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015561

Secondary Accession Numbers

HMDB15561

Metabolite Identification

Common Name

Zuclopenthixol

Description

Zuclopenthixol is only found in individuals that have used or taken this drug. It is a thioxanthene with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors. [PubChem]Zuclopenthixol is a typical antipsychotic neuroleptic drug of the thioxanthene group. It mainly acts by antagonism of D1 and D2 dopamine receptors. Zuclopenthixol also has high affinity for alpha1-adrenergic and 5-HT2 receptors. It has weaker histamine H1 receptor blocking activity, and even lower affinity for muscarinic cholinergic and alpha2-adrenergic receptors.

Structure

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

1624
  Mrv0541 02231215362D          

 27 30  0  0  0  0            999 V2000
    6.7619   -1.8715    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -3.5415    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363    3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    0.5835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    1.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -3.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -3.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -1.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -1.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 13  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END

HMDB0015561
     RDKit          3D
Zuclopenthixol
 52 55  0  0  0  0  0  0  0  0999 V2000
    7.9769    0.0638    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -0.1129   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.3962    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941   -0.6016    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    0.5492   -0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    0.3200   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    0.2374    0.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5235    0.7764    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -0.0330   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    0.7366   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    0.3091   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.3106    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    2.6422    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    3.6751    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9313    3.3182    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3024    1.9943    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3567    1.0160    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.6915    0.3730 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -1.6493   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8475   -2.9356   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -3.7700   -1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -3.2757   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.3405   -1.9168 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -1.9539   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -1.1131   -0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924   -0.1955    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -1.2513    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6850    0.2645    1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -1.0043   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706    0.8057   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879   -1.3649    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    0.3662    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399    0.8083   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886    1.4637    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    1.1373   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608   -0.6096   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652    1.8128   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    0.7484    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0531    0.0446   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -0.9731    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.8409   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    3.0262   -0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    4.7218    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7021    4.0586    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3475    1.6929    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389   -3.3672   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -4.7986   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -1.6874   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -0.5843    2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018    0.7019    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -2.0209    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -1.7121    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 20 46  1  0
 21 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

1624
  Mrv0541 02231215362D          

 27 30  0  0  0  0            999 V2000
    6.7619   -1.8715    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -3.5415    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363    3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    0.5835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    1.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -3.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -3.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -1.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -1.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 13  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015561

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-

> <INCHI_KEY>
WFPIAZLQTJBIFN-DVZOWYKESA-N

> <FORMULA>
C22H25ClN2OS

> <MOLECULAR_WEIGHT>
400.965

> <EXACT_MASS>
400.137611829

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.28789200955396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
4.22298393

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.59309817131956

> <JCHEM_PKA_STRONGEST_BASIC>
8.427567970053593

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
127.00030000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zuclopenthixol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015561
     RDKit          3D
Zuclopenthixol
 52 55  0  0  0  0  0  0  0  0999 V2000
    7.9769    0.0638    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -0.1129   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.3962    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941   -0.6016    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    0.5492   -0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    0.3200   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    0.2374    0.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5235    0.7764    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -0.0330   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    0.7366   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    0.3091   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.3106    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    2.6422    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    3.6751    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9313    3.3182    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3024    1.9943    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3567    1.0160    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.6915    0.3730 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -1.6493   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8475   -2.9356   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -3.7700   -1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -3.2757   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.3405   -1.9168 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -1.9539   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -1.1131   -0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924   -0.1955    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -1.2513    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6850    0.2645    1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -1.0043   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706    0.8057   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879   -1.3649    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    0.3662    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399    0.8083   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886    1.4637    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    1.1373   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608   -0.6096   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652    1.8128   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    0.7484    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0531    0.0446   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -0.9731    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.8409   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    3.0262   -0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    4.7218    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7021    4.0586    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3475    1.6929    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389   -3.3672   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -4.7986   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -1.6874   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -0.5843    2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018    0.7019    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -2.0209    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -1.7121    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 20 46  1  0
 21 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1624                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      12.622  -3.493   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       7.186  -6.611   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      15.188   5.709   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.853   1.089   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.520   2.629   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.853   2.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.187   0.319   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.187   3.399   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.520   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.519   0.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.854   3.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.519  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854   4.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.186  -1.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.186  -3.531   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.519  -4.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.852  -4.301   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.519  -5.841   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.852  -5.841   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.896  -3.477   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.475  -3.477   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.896  -6.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.475  -6.664   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -4.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -4.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.873   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -5.873   0.000  0.00  0.00           C+0
CONECT    1   24                                                            
CONECT    2   18   19                                                       
CONECT    3   13                                                            
CONECT    4    6    7   10                                                  
CONECT    5    8    9   11                                                  
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    5    6                                                       
CONECT    9    5    7                                                       
CONECT   10    4   12                                                       
CONECT   11    5   13                                                       
CONECT   12   10   14                                                       
CONECT   13    3   11                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   18   20                                                  
CONECT   17   15   19   21                                                  
CONECT   18    2   16   22                                                  
CONECT   19    2   17   23                                                  
CONECT   20   16   24                                                       
CONECT   21   17   25                                                       
CONECT   22   18   26                                                       
CONECT   23   19   27                                                       
CONECT   24    1   20   26                                                  
CONECT   25   21   27                                                       
CONECT   26   22   24                                                       
CONECT   27   23   25                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0015561
HETATM    1  O1  UNL     1       7.977   0.064   0.852  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.895  -0.113  -0.010  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.678  -0.396   0.841  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.494  -0.602   0.077  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.983   0.549  -0.609  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.514   0.320  -1.021  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.790   0.237   0.175  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.524   0.776   0.286  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.551  -0.033  -0.617  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.752   0.737  -0.328  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.992   0.309  -0.279  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.060   1.311   0.075  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.708   2.642   0.086  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.630   3.675   0.297  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.931   3.318   0.499  1.00  0.00           C  
HETATM   16  C13 UNL     1      -6.302   1.994   0.492  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.357   1.016   0.281  1.00  0.00           C  
HETATM   18  S1  UNL     1      -5.905  -0.692   0.373  1.00  0.00           S  
HETATM   19  C15 UNL     1      -4.565  -1.649  -0.263  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.848  -2.936  -0.570  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.894  -3.770  -1.074  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.646  -3.276  -1.266  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -1.409  -4.341  -1.917  1.00  0.00          CL  
HETATM   24  C19 UNL     1      -2.313  -1.954  -0.965  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.268  -1.113  -0.452  1.00  0.00           C  
HETATM   26  C21 UNL     1       2.492  -0.195   1.324  1.00  0.00           C  
HETATM   27  C22 UNL     1       3.504  -1.251   0.905  1.00  0.00           C  
HETATM   28  H1  UNL     1       7.685   0.264   1.764  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.113  -1.004  -0.636  1.00  0.00           H  
HETATM   30  H3  UNL     1       6.771   0.806  -0.615  1.00  0.00           H  
HETATM   31  H4  UNL     1       5.888  -1.365   1.370  1.00  0.00           H  
HETATM   32  H5  UNL     1       5.582   0.366   1.651  1.00  0.00           H  
HETATM   33  H6  UNL     1       4.540   0.808  -1.528  1.00  0.00           H  
HETATM   34  H7  UNL     1       3.989   1.464   0.039  1.00  0.00           H  
HETATM   35  H8  UNL     1       2.260   1.137  -1.705  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.561  -0.610  -1.624  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.465   1.813  -0.066  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.160   0.748   1.325  1.00  0.00           H  
HETATM   39  H12 UNL     1      -0.053   0.045  -1.552  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.409  -0.973   0.000  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.590   1.841  -0.116  1.00  0.00           H  
HETATM   42  H15 UNL     1      -2.693   3.026  -0.077  1.00  0.00           H  
HETATM   43  H16 UNL     1      -4.323   4.722   0.300  1.00  0.00           H  
HETATM   44  H17 UNL     1      -6.702   4.059   0.667  1.00  0.00           H  
HETATM   45  H18 UNL     1      -7.347   1.693   0.654  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.839  -3.367  -0.431  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.105  -4.799  -1.320  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.371  -1.687  -1.255  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.806  -0.584   2.106  1.00  0.00           H  
HETATM   50  H23 UNL     1       3.002   0.702   1.785  1.00  0.00           H  
HETATM   51  H24 UNL     1       2.938  -2.021   0.348  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.954  -1.712   1.807  1.00  0.00           H  
CONECT    1    2   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   27
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   26
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   11   41
CONECT   11   12   25
CONECT   12   13   13   17
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   25
CONECT   20   21   46
CONECT   21   22   22   47
CONECT   22   23   24
CONECT   24   25   25   48
CONECT   26   27   49   50
CONECT   27   51   52
END

HMDB0015561
     RDKit          3D
Zuclopenthixol
 52 55  0  0  0  0  0  0  0  0999 V2000
    7.9769    0.0638    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -0.1129   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.3962    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941   -0.6016    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    0.5492   -0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    0.3200   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    0.2374    0.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5235    0.7764    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -0.0330   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    0.7366   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    0.3091   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.3106    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    2.6422    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    3.6751    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9313    3.3182    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3024    1.9943    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3567    1.0160    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.6915    0.3730 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -1.6493   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8475   -2.9356   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -3.7700   -1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -3.2757   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.3405   -1.9168 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -1.9539   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -1.1131   -0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924   -0.1955    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -1.2513    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6850    0.2645    1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -1.0043   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706    0.8057   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879   -1.3649    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    0.3662    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399    0.8083   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886    1.4637    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    1.1373   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608   -0.6096   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652    1.8128   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    0.7484    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0531    0.0446   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -0.9731    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.8409   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    3.0262   -0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    4.7218    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7021    4.0586    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3475    1.6929    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389   -3.3672   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -4.7986   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -1.6874   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -0.5843    2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018    0.7019    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -2.0209    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -1.7121    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  7 26  1  0
 26 27  1  0
 27  4  1  0
 25 11  1  0
 17 12  1  0
 25 19  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 20 46  1  0
 21 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol	ChEBI
Zuclopenthixolum	ChEBI
Zuclopentixol	ChEBI
Clopixol	Kegg
Zuclopenthixol acetate	HMDB
Zuclopenthixol decanoate	HMDB
Zuclopenthixol dihydrochloride	HMDB
alpha Clopenthixol	HMDB
alpha-Clopenthixol	HMDB
Clopenthixol	HMDB
Cisordinol	HMDB

Chemical Formula

C₂₂H₂₅ClN₂OS

Average Molecular Weight

400.965

Monoisotopic Molecular Weight

400.137611829

IUPAC Name

2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol

Traditional Name

zuclopenthixol

CAS Registry Number

53772-83-1

SMILES

OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1

InChI Identifier

InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-

InChI Key

WFPIAZLQTJBIFN-DVZOWYKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiopyrans

Sub Class

1-benzothiopyrans

Direct Parent

Thioxanthenes

Alternative Parents

Substituents

Thioxanthene
Diarylthioether
Aryl thioether
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Azacycle
Thioether
Alkanolamine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Alcohol
Primary alcohol
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

clopenthixol (CHEBI:51364 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015561)

Source

Exogenous

Exogenous (HMDB: HMDB0015561)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0026 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	194.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	4.46	ALOGPS
logP	4.22	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	8.43	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	5	ChemAxon
Refractivity	127 m³·mol⁻¹	ChemAxon
Polarizability	45.29 Å³	ChemAxon
Number of Rings	4	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]+	196.486	30932474
DeepCCS	[M-H]-	194.029	30932474
DeepCCS	[M-2H]-	228.523	30932474
DeepCCS	[M+Na]+	203.876	30932474
AllCCS	[M+H]+	194.5	32859911
AllCCS	[M+H-H2O]+	191.9	32859911
AllCCS	[M+NH4]+	196.8	32859911
AllCCS	[M+Na]+	197.4	32859911
AllCCS	[M-H]-	193.9	32859911
AllCCS	[M+Na-2H]-	193.9	32859911
AllCCS	[M+HCOO]-	194.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.7 minutes	32390414
Predicted by Siyang on May 30, 2022	10.73 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.74 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	113.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1089.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	482.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	547.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	918.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1016.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	217.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zuclopenthixol	OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	4476.8	Standard polar	33892256
Zuclopenthixol	OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	3234.4	Standard non polar	33892256
Zuclopenthixol	OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1	3160.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zuclopenthixol,1TMS,isomer #1	C[Si](C)(C)OCCN1CCN(CC/C=C2/C3=CC=CC=C3SC3=CC=C(Cl)C=C23)CC1	3447.0	Semi standard non polar	33892256
Zuclopenthixol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN1CCN(CC/C=C2/C3=CC=CC=C3SC3=CC=C(Cl)C=C23)CC1	3682.4	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 - Zuclopenthixol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9634000000-725d867abc3a21a8367b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zuclopenthixol GC-MS (1 TMS) - 70eV, Positive	splash10-0gi0-9344200000-75820d187d1501e996b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zuclopenthixol 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 - Zuclopenthixol 10V, Positive-QTOF	splash10-0udi-0122900000-b0c208380aecf467bf42	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 20V, Positive-QTOF	splash10-0fl0-3797300000-6a0d6b81802987061025	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 40V, Positive-QTOF	splash10-022j-9742000000-32dbb76748579ce3b574	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 10V, Negative-QTOF	splash10-0002-0009000000-111f43ef21dddab4b92a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 20V, Negative-QTOF	splash10-0002-1309000000-5ad402c11e1d57ff2c3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 40V, Negative-QTOF	splash10-0006-9200000000-4957e4a977f2522244e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 10V, Positive-QTOF	splash10-0udi-0000900000-c8fc2efcbee8e9787417	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 20V, Positive-QTOF	splash10-0uk9-0173900000-88227a1c47ee94c13262	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 40V, Positive-QTOF	splash10-0c00-1498000000-7582c437e09f5a3c3e63	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 10V, Negative-QTOF	splash10-0002-0009000000-f42087d0e1f36c98fd92	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 20V, Negative-QTOF	splash10-00kb-0009000000-de6822a024bc2597f5b7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zuclopenthixol 40V, Negative-QTOF	splash10-0pb9-1059000000-01d717517b320d6b747f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB01624	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01624	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01624

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zuclopenthixol

METLIN ID

Not Available

PubChem Compound

5311507

PDB ID

Not Available

ChEBI ID

51364

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

Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. [PubMed:12957216 ]
Khalifa AE: Pro-oxidant activity of zuclopenthixol in vivo: differential effect of the drug on brain oxidative status of scopolamine-treated rats. Hum Exp Toxicol. 2004 Aug;23(9):439-45. [PubMed:15497819 ]
Jayakody K, Gibson RC, Kumar A, Gunadasa S: Zuclopenthixol acetate for acute schizophrenia and similar serious mental illnesses. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD000525. doi: 10.1002/14651858.CD000525.pub3. [PubMed:22513898 ]
Nielsen MK, Johansen SS: Simultaneous determination of 25 common pharmaceuticals in whole blood using ultra-performance liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Sep;36(7):497-506. doi: 10.1093/jat/bks054. Epub 2012 Jun 19. [PubMed:22718540 ]
Fond G, Macgregor A, Tamouza R, Hamdani N, Meary A, Leboyer M, Dubremetz JF: Comparative analysis of anti-toxoplasmic activity of antipsychotic drugs and valproate. Eur Arch Psychiatry Clin Neurosci. 2014 Mar;264(2):179-83. doi: 10.1007/s00406-013-0413-4. Epub 2013 Jun 15. [PubMed:23771405 ]
Internet Mental Health [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. [PubMed:12957216 ]

Enzyme Details

3. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Gareri P, De Fazio P, Stilo M, Ferreri G, De Sarro G: Conventional and atypical antipsychotics in the elderly : a review. Clin Drug Investig. 2003;23(5):287-322. [PubMed:17535043 ]
Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. [PubMed:1822319 ]
Nyberg S, Farde L, Bartfai A, Halldin C: Central D2 receptor occupancy and effects of zuclopenthixol acetate in humans. Int Clin Psychopharmacol. 1995 Nov;10(4):221-7. [PubMed:8748043 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Nyberg S, Farde L, Bartfai A, Halldin C: Central D2 receptor occupancy and effects of zuclopenthixol acetate in humans. Int Clin Psychopharmacol. 1995 Nov;10(4):221-7. [PubMed:8748043 ]
Gjerden P, Slordal L, Bramness JG: Association between the use of anticholinergic antiparkinson drugs and safety and receptor drug-binding profiles of antipsychotic agents. Eur J Clin Pharmacol. 2009 Dec;65(12):1229-35. doi: 10.1007/s00228-009-0696-6. [PubMed:19644682 ]
Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. [PubMed:12957216 ]

Enzyme Details

5. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. [PubMed:12957216 ]

Enzyme Details

6. D(1A) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. [PubMed:1822319 ]
Manzaneque JM, Navarro JF: An ethopharmacological assessment of the effects of zuclopenthixol on agonistic interactions in male mice. Methods Find Exp Clin Pharmacol. 1999 Jan-Feb;21(1):11-5. [PubMed:10222441 ]

Enzyme Details

7. D(1B) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: DRD5
Uniprot ID:: P21918
Molecular weight:: 52950.5

References

Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. [PubMed:1822319 ]
Manzaneque JM, Navarro JF: An ethopharmacological assessment of the effects of zuclopenthixol on agonistic interactions in male mice. Methods Find Exp Clin Pharmacol. 1999 Jan-Feb;21(1):11-5. [PubMed:10222441 ]

Showing metabocard for Zuclopenthixol (HMDB0015561)

MOL for HMDB0015561 (Zuclopenthixol)

3D MOL for HMDB0015561 (Zuclopenthixol)

3D SDF for HMDB0015561 (Zuclopenthixol)

3D-SDF for HMDB0015561 (Zuclopenthixol)

PDB for HMDB0015561 (Zuclopenthixol)

3D PDB for HMDB0015561 (Zuclopenthixol)

SMILES for HMDB0015561 (Zuclopenthixol)

INCHI for HMDB0015561 (Zuclopenthixol)

Structure for HMDB0015561 (Zuclopenthixol)

3D Structure for HMDB0015561 (Zuclopenthixol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References