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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015013

Secondary Accession Numbers

HMDB15013

Metabolite Identification

Common Name

Flupenthixol

Description

Flupenthixol 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. Its primary use is as a long acting injection given two or three weekly to people with schizophrenia who have a poor compliance with medication and suffer frequent relapses of illness. Flupenthixol is a very strong basic compound (based on its pKa). Flupenthixol is a potentially toxic compound. It's antipsychotic activity is thought to be related to blocks postsynaptic dopamine receptors in the CNS. Flupenthixol is an antipsychotic neuroleptic drug. It is a thioxanthene, and therefore closely related to the phenothiazines. It is a D1 and D2 receptor antagonist.

Structure

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


  Mrv0541 04191212152D          

 31 34  0  0  0  0            999 V2000
   -1.9152   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -1.5027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    2.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    3.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716    3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8006    3.8598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572    0.9723    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.5598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -0.0662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    1.5557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END

HMDB0015013
     RDKit          3D
Flupenthixol
 57 60  0  0  0  0  0  0  0  0999 V2000
   -7.4534    0.8111    0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2429    1.4197    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2705    0.5234   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9253   -0.6674    0.5981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1530   -0.4552    1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    0.3561    1.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324   -0.1790    0.4043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.9113   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840    0.5428   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.4749   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -0.3985   -0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    0.8503   -1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924    2.0320   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559    3.1682   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    3.1416   -1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.9366   -2.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    0.8190   -2.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8225   -0.8312   -2.7965 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -1.9828   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -2.1364   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -1.9661    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -1.5932    1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -1.4024    2.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -1.0697    3.5176 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -2.5167    3.3360 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6733   -0.2966    2.9038 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -1.4370    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -1.6032   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.9369   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4844   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9521    1.2725    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4647    2.2665   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8556    1.8696    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    0.1913   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837    1.0905   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7924   -1.4520    2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.0053    2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    0.4778    2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.4160    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    1.3297    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    1.7054   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    0.0922   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    1.4246   -1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.4634   -0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982    2.0138    0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901    4.1200   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    4.0477   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9918    1.8452   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -3.0203   -1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -2.4147   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522   -2.0806    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -1.1574    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270   -2.4554   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -1.7972   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -0.2691   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -1.6359   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -2.4916    0.1785 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  3
 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  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  2  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 30  4  1  0
 28 11  1  0
 17 12  1  0
 28 19  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
M  END


  Mrv0541 04191212152D          

 31 34  0  0  0  0            999 V2000
   -1.9152   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -1.5027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    2.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    3.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716    3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8006    3.8598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572    0.9723    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.5598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -0.0662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    1.5557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015013

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2SC2=C1C=CC=C2)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C23H27F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,20,22,29H,3,9-15H2

> <INCHI_KEY>
DTTVNHWDONBIKE-UHFFFAOYSA-N

> <FORMULA>
C23H27F3N2OS

> <MOLECULAR_WEIGHT>
436.533

> <EXACT_MASS>
436.179618801

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.277775890784596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{3-[2-(trifluoromethyl)-9,9a-dihydro-4aH-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.5415254790000006

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.593098177428736

> <JCHEM_PKA_STRONGEST_BASIC>
8.50878038318509

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
120.93129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flupenthixol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015013
     RDKit          3D
Flupenthixol
 57 60  0  0  0  0  0  0  0  0999 V2000
   -7.4534    0.8111    0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2429    1.4197    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2705    0.5234   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9253   -0.6674    0.5981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1530   -0.4552    1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    0.3561    1.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324   -0.1790    0.4043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.9113   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840    0.5428   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.4749   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -0.3985   -0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    0.8503   -1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924    2.0320   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559    3.1682   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    3.1416   -1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.9366   -2.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    0.8190   -2.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8225   -0.8312   -2.7965 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -1.9828   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -2.1364   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -1.9661    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -1.5932    1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -1.4024    2.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -1.0697    3.5176 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -2.5167    3.3360 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6733   -0.2966    2.9038 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -1.4370    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -1.6032   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.9369   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4844   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9521    1.2725    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4647    2.2665   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8556    1.8696    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    0.1913   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837    1.0905   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7924   -1.4520    2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.0053    2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    0.4778    2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.4160    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    1.3297    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    1.7054   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    0.0922   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    1.4246   -1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.4634   -0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982    2.0138    0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901    4.1200   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    4.0477   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9918    1.8452   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -3.0203   -1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -2.4147   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522   -2.0806    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -1.1574    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270   -2.4554   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -1.7972   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -0.2691   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -1.6359   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -2.4916    0.1785 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  3
 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  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  2  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 30  4  1  0
 28 11  1  0
 17 12  1  0
 28 19  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -3.575  -0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.909   0.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.243  -0.495   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.243  -2.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.909  -2.805   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.575  -2.035   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -2.241  -2.805   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      -0.908  -2.035   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.908  -0.495   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.241   0.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.426   0.275   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.426  -2.805   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.760  -2.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.760  -0.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.241   1.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.908   2.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.908   4.125   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.426   4.895   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.760   7.205   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.426   6.435   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.760   4.125   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.093   4.895   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       3.093   6.435   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       4.427   7.205   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.761   6.435   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.094   7.205   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.093   0.275   0.000  0.00  0.00           C+0
HETATM   28  F   UNK     0       3.093   1.815   0.000  0.00  0.00           F+0
HETATM   29  F   UNK     0       4.427   1.045   0.000  0.00  0.00           F+0
HETATM   30  F   UNK     0       4.581  -0.124   0.000  0.00  0.00           F+0
HETATM   31  H   UNK     0      -3.330   2.904   0.000  0.00  0.00           H+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9   10   11    8                                                  
CONECT   10    1    9   15                                                  
CONECT   11    9   14                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   11   13   27                                                  
CONECT   15   10   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   20   21                                                  
CONECT   19   20   23                                                       
CONECT   20   18   19                                                       
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   19   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   14   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0015013
HETATM    1  O1  UNL     1      -7.453   0.811   0.855  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.243   1.420   0.595  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.270   0.523  -0.110  1.00  0.00           C  
HETATM    4  N1  UNL     1      -4.925  -0.667   0.598  1.00  0.00           N  
HETATM    5  C3  UNL     1      -4.153  -0.455   1.790  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.957   0.356   1.447  1.00  0.00           C  
HETATM    7  N2  UNL     1      -2.132  -0.179   0.404  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.325   0.911  -0.087  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.384   0.543  -1.176  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.608  -0.475  -0.812  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.917  -0.399  -0.794  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.557   0.850  -1.168  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.192   2.032  -0.573  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.856   3.168  -0.972  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.863   3.142  -1.943  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.219   1.937  -2.536  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.570   0.819  -2.147  1.00  0.00           C  
HETATM   18  S1  UNL     1       3.823  -0.831  -2.797  1.00  0.00           S  
HETATM   19  C15 UNL     1       3.739  -1.983  -1.368  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.105  -2.136  -0.858  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.438  -1.966   0.377  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.428  -1.593   1.375  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.834  -1.402   2.816  1.00  0.00           C  
HETATM   24  F1  UNL     1       3.695  -1.070   3.518  1.00  0.00           F  
HETATM   25  F2  UNL     1       5.425  -2.517   3.336  1.00  0.00           F  
HETATM   26  F3  UNL     1       5.673  -0.297   2.904  1.00  0.00           F  
HETATM   27  C20 UNL     1       3.204  -1.437   0.988  1.00  0.00           C  
HETATM   28  C21 UNL     1       2.731  -1.603  -0.397  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.783  -0.937  -0.594  1.00  0.00           C  
HETATM   30  C23 UNL     1      -4.122  -1.484  -0.281  1.00  0.00           C  
HETATM   31  H1  UNL     1      -7.952   1.272   1.575  1.00  0.00           H  
HETATM   32  H2  UNL     1      -6.465   2.266  -0.115  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.856   1.870   1.511  1.00  0.00           H  
HETATM   34  H4  UNL     1      -5.780   0.191  -1.060  1.00  0.00           H  
HETATM   35  H5  UNL     1      -4.384   1.091  -0.457  1.00  0.00           H  
HETATM   36  H6  UNL     1      -3.792  -1.452   2.128  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.705  -0.005   2.613  1.00  0.00           H  
HETATM   38  H8  UNL     1      -2.359   0.478   2.396  1.00  0.00           H  
HETATM   39  H9  UNL     1      -3.209   1.416   1.171  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.760   1.330   0.764  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.023   1.705  -0.418  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.931   0.092  -2.064  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.106   1.425  -1.600  1.00  0.00           H  
HETATM   44  H14 UNL     1       0.216  -1.463  -0.490  1.00  0.00           H  
HETATM   45  H15 UNL     1       1.398   2.014   0.184  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.590   4.120  -0.520  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.371   4.048  -2.240  1.00  0.00           H  
HETATM   48  H18 UNL     1       4.992   1.845  -3.295  1.00  0.00           H  
HETATM   49  H19 UNL     1       3.436  -3.020  -1.836  1.00  0.00           H  
HETATM   50  H20 UNL     1       5.927  -2.415  -1.545  1.00  0.00           H  
HETATM   51  H21 UNL     1       6.452  -2.081   0.760  1.00  0.00           H  
HETATM   52  H22 UNL     1       2.484  -1.157   1.787  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.927  -2.455  -0.349  1.00  0.00           H  
HETATM   54  H24 UNL     1      -2.111  -1.797  -0.888  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.911  -0.269  -1.500  1.00  0.00           H  
HETATM   56  H26 UNL     1      -4.750  -1.636  -1.205  1.00  0.00           H  
HETATM   57  H27 UNL     1      -4.041  -2.492   0.178  1.00  0.00           H  
CONECT    1    2   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   30
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   29
CONECT    8    9   40   41
CONECT    9   10   42   43
CONECT   10   11   11   44
CONECT   11   12   28
CONECT   12   13   13   17
CONECT   13   14   45
CONECT   14   15   15   46
CONECT   15   16   47
CONECT   16   17   17   48
CONECT   17   18
CONECT   18   19
CONECT   19   20   28   49
CONECT   20   21   21   50
CONECT   21   22   51
CONECT   22   23   27   27
CONECT   23   24   25   26
CONECT   27   28   52
CONECT   28   53
CONECT   29   30   54   55
CONECT   30   56   57
END

HMDB0015013
     RDKit          3D
Flupenthixol
 57 60  0  0  0  0  0  0  0  0999 V2000
   -7.4534    0.8111    0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2429    1.4197    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2705    0.5234   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9253   -0.6674    0.5981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1530   -0.4552    1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    0.3561    1.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324   -0.1790    0.4043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.9113   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840    0.5428   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.4749   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -0.3985   -0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    0.8503   -1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924    2.0320   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559    3.1682   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    3.1416   -1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.9366   -2.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    0.8190   -2.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8225   -0.8312   -2.7965 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -1.9828   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -2.1364   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -1.9661    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -1.5932    1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -1.4024    2.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -1.0697    3.5176 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -2.5167    3.3360 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6733   -0.2966    2.9038 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -1.4370    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -1.6032   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.9369   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4844   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9521    1.2725    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4647    2.2665   -0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8556    1.8696    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    0.1913   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837    1.0905   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7924   -1.4520    2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.0053    2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    0.4778    2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.4160    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    1.3297    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    1.7054   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    0.0922   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    1.4246   -1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.4634   -0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982    2.0138    0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901    4.1200   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    4.0477   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9918    1.8452   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -3.0203   -1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -2.4147   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522   -2.0806    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -1.1574    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270   -2.4554   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -1.7972   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -0.2691   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -1.6359   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -2.4916    0.1785 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  3
 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  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  2  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 30  4  1  0
 28 11  1  0
 17 12  1  0
 28 19  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Trifluoromethyl-9-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propylidene)thioxanthene	ChEBI
2-Trifluoromethyl-9-(3-(4-(beta-hydroxyethyl)-1-piperazinyl)propylidene)thioxanthene	ChEBI
4-(3-(2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)-1-piperazineethanol	ChEBI
4-(3-(2-(Trifluoromethyl)thioxanthen-9-ylidene)propyl)-1-piperazineethanol	ChEBI
Flupentixol	ChEBI
Flupentixolum	ChEBI
2-Trifluoromethyl-9-(3-(4-(b-hydroxyethyl)-1-piperazinyl)propylidene)thioxanthene	Generator
2-Trifluoromethyl-9-(3-(4-(β-hydroxyethyl)-1-piperazinyl)propylidene)thioxanthene	Generator
Flupenthixole	HMDB

Chemical Formula

C₂₃H₂₇F₃N₂OS

Average Molecular Weight

436.533

Monoisotopic Molecular Weight

436.179618801

IUPAC Name

2-(4-{3-[2-(trifluoromethyl)-9,9a-dihydro-4aH-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol

Traditional Name

flupenthixol

CAS Registry Number

2709-56-0

SMILES

[H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2SC2=C1C=CC=C2)C(F)(F)F

InChI Identifier

InChI=1S/C23H27F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,20,22,29H,3,9-15H2

InChI Key

DTTVNHWDONBIKE-UHFFFAOYSA-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
Thiochromane
Aryl thioether
N-alkylpiperazine
Alkylarylthioether
1,4-diazinane
Piperazine
Thiopyran
Benzenoid
Tertiary aliphatic amine
1,2-aminoalcohol
Tertiary amine
Azacycle
Alkanolamine
Thioether
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Amine
Alkyl halide
Organopnictogen compound
Alkyl fluoride
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

primary alcohol (CHEBI:5121 )
N-alkylpiperazine (CHEBI:5121 )
thioxanthenes (CHEBI:5121 )
fluorine molecular entity (CHEBI:5121 )

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: HMDB0015013)

Source

Exogenous

Exogenous (HMDB: HMDB0015013)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.003 g/L	Not Available
LogP	4.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	4.12	ALOGPS
logP	3.54	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	8.51	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	6	ChemAxon
Refractivity	120.93 m³·mol⁻¹	ChemAxon
Polarizability	45.28 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	192.099	30932474
DeepCCS	[M-H]-	189.741	30932474
DeepCCS	[M-2H]-	223.89	30932474
DeepCCS	[M+Na]+	199.483	30932474
AllCCS	[M+H]+	202.2	32859911
AllCCS	[M+H-H2O]+	200.0	32859911
AllCCS	[M+NH4]+	204.2	32859911
AllCCS	[M+Na]+	204.8	32859911
AllCCS	[M-H]-	198.8	32859911
AllCCS	[M+Na-2H]-	199.1	32859911
AllCCS	[M+HCOO]-	199.6	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.	3.63 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9635 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	85.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1378.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	186.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	406.4 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	488.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	504.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1096.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	355.3 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	927.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	297.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	325.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	535.9 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	28.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flupenthixol	[H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2SC2=C1C=CC=C2)C(F)(F)F	4438.2	Standard polar	33892256
Flupenthixol	[H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2SC2=C1C=CC=C2)C(F)(F)F	3092.6	Standard non polar	33892256
Flupenthixol	[H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2SC2=C1C=CC=C2)C(F)(F)F	2975.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flupenthixol,1TMS,isomer #1	C[Si](C)(C)OCCN1CCN(CCC=C2C3=CC=CC=C3SC3C=CC(C(F)(F)F)=CC23)CC1	3093.8	Semi standard non polar	33892256
Flupenthixol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN1CCN(CCC=C2C3=CC=CC=C3SC3C=CC(C(F)(F)F)=CC23)CC1	3304.7	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 - Flupenthixol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9676500000-6b1399e0dd965860c60c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flupenthixol GC-MS (1 TMS) - 70eV, Positive	splash10-0kfx-7343900000-bb450af2259a54640db1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flupenthixol 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 - Flupenthixol 10V, Positive-QTOF	splash10-000i-0201900000-095389998f2b63d484e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 20V, Positive-QTOF	splash10-0aor-1914300000-8295bd965255669954f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 40V, Positive-QTOF	splash10-015i-4901000000-783ed0fccbbc28c48cee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 10V, Negative-QTOF	splash10-000i-0000900000-9ce18246bedc83edf347	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 20V, Negative-QTOF	splash10-000i-1401900000-aee927a7c2a7b4e811f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 40V, Negative-QTOF	splash10-0006-9201000000-b5c6ccae989978ac9b0e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 10V, Positive-QTOF	splash10-000i-0001900000-bd4e09974af0466a3cbe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 20V, Positive-QTOF	splash10-052r-0016900000-5c47058a37461c2bef3d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 40V, Positive-QTOF	splash10-0zfs-2239000000-6f83d85a09b5c5a4753e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 10V, Negative-QTOF	splash10-000i-0000900000-1edd1377901f27944317	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 20V, Negative-QTOF	splash10-0a4u-0005900000-4d71ee0a497e6c0b2468	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flupenthixol 40V, Negative-QTOF	splash10-0006-0295100000-6274c7e3ec4279e237fd	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 DB00875	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00875	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

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

Flupentixol

METLIN ID

Not Available

PubChem Compound

25137855

PDB ID

Not Available

ChEBI ID

5121

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

Enzymes

Enzyme Details

1. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

References

Zhu MY, Juorio AV, Paterson IA, Boulton AA: Regulation of aromatic L-amino acid decarboxylase in rat striatal synaptosomes: effects of dopamine receptor agonists and antagonists. Br J Pharmacol. 1994 May;112(1):23-30. [PubMed:7913379 ]

Enzyme Details

2. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Ogren SO, Hall H, Kohler C, Magnusson O, Lindbom LO, Angeby K, Florvall L: Remoxipride, a new potential antipsychotic compound with selective antidopaminergic actions in the rat brain. Eur J Pharmacol. 1984 Jul 20;102(3-4):459-74. [PubMed:6149133 ]
Arnt J: Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. Eur J Pharmacol. 1995 Sep 5;283(1-3):55-62. [PubMed:7498321 ]
Huettl P, Gerhardt GA, Browning MD, Masserano JM: Effects of dopamine receptor agonists and antagonists on catecholamine release in bovine chromaffin cells. J Pharmacol Exp Ther. 1991 May;257(2):567-74. [PubMed:1674528 ]
Nilsson CL, Ekman A, Hellstrand M, Eriksson E: Inverse agonism at dopamine D2 receptors. Haloperidol-induced prolactin release from GH4C1 cells transfected with the human D2 receptor is antagonized by R(-)-n-propylnorapomorphine, raclopride, and phenoxybenzamine. Neuropsychopharmacology. 1996 Jul;15(1):53-61. [PubMed:8797192 ]
Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172 ]

Enzyme Details

3. 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

Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172 ]

Enzyme Details

4. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Cai G, Gurdal H, Smith C, Wang HY, Friedman E: Inverse agonist properties of dopaminergic antagonists at the D(1A) dopamine receptor: uncoupling of the D(1A) dopamine receptor from G(s) protein. Mol Pharmacol. 1999 Nov;56(5):989-96. [PubMed:10531405 ]
Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H: Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl). 2007 Feb;190(2):241-9. Epub 2006 Nov 17. [PubMed:17111172 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Hait WN, Gesmonde JF, Murren JR, Yang JM, Chen HX, Reiss M: Terfenadine (Seldane): a new drug for restoring sensitivity to multidrug resistant cancer cells. Biochem Pharmacol. 1993 Jan 26;45(2):401-6. [PubMed:8094615 ]
Dey S, Hafkemeyer P, Pastan I, Gottesman MM: A single amino acid residue contributes to distinct mechanisms of inhibition of the human multidrug transporter by stereoisomers of the dopamine receptor antagonist flupentixol. Biochemistry. 1999 May 18;38(20):6630-9. [PubMed:10350482 ]
Hafkemeyer P, Licht T, Pastan I, Gottesman MM: Chemoprotection of hematopoietic cells by a mutant P-glycoprotein resistant to a potent chemosensitizer of multidrug-resistant cancers. Hum Gene Ther. 2000 Mar 1;11(4):555-65. [PubMed:10724034 ]
Yang JM, Vassil A, Hait WN: Involvement of phosphatidylinositol-3-kinase in membrane ruffling induced by P-glycoprotein substrates in multidrug-resistant carcinoma cells. Biochem Pharmacol. 2002 Mar 1;63(5):959-66. [PubMed:11911848 ]
Ford JM, Bruggemann EP, Pastan I, Gottesman MM, Hait WN: Cellular and biochemical characterization of thioxanthenes for reversal of multidrug resistance in human and murine cell lines. Cancer Res. 1990 Mar 15;50(6):1748-56. [PubMed:1968358 ]
Ford JM, Yang JM, Hait WN: Effect of buthionine sulfoximine on toxicity of verapamil and doxorubicin to multidrug resistant cells and to mice. Cancer Res. 1991 Jan 1;51(1):67-72. [PubMed:1988108 ]

Showing metabocard for Flupenthixol (HMDB0015013)

MOL for HMDB0015013 (Flupenthixol)

3D MOL for HMDB0015013 (Flupenthixol)

3D SDF for HMDB0015013 (Flupenthixol)

3D-SDF for HMDB0015013 (Flupenthixol)

PDB for HMDB0015013 (Flupenthixol)

3D PDB for HMDB0015013 (Flupenthixol)

SMILES for HMDB0015013 (Flupenthixol)

INCHI for HMDB0015013 (Flupenthixol)

Structure for HMDB0015013 (Flupenthixol)

3D Structure for HMDB0015013 (Flupenthixol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References