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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (1) Show 10 proteins XML

enzymes (9)transporters (1) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014969

Secondary Accession Numbers

HMDB14969

Metabolite Identification

Common Name

Trifluoperazine

Description

Trifluoperazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine. It is used as an antipsychotic and an antiemetic. [PubChem]Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

Structure

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

831
  Mrv0541 02231215022D          

 28 31  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 28  1  0  0  0  0
  4 28  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  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 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 25  2  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

HMDB0014969
     RDKit          3D
Trifluoperazine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0789    0.4002   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.0417   -0.3270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.9817    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -0.3102    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.0260    0.7880 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.9871    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -0.8014    1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -0.5618   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0545   -0.5124   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.7579    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -2.9316    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013   -4.1476    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169   -4.2306    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -3.0653    1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -1.8645    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9527   -0.4389    0.8320 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714    0.8988    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    2.0472   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560    3.1120   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    2.9674   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    4.0983   -1.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172    3.7156   -3.1158 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    5.1809   -1.9471 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902    4.5112   -1.1104 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258    1.7873   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    0.6985   -0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.3772   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352    0.3554   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    1.1306   -0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.0525    0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -0.4464   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.8386    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.9017    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -0.4582    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -1.1313    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.9966    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.1585    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.5043    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.2069    1.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    0.4534   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -1.3114   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -2.8716   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -5.0502    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1550   -5.1802    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4913   -3.1298    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389    2.0939    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7096    4.0349   -1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.8103   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428   -0.3219   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    1.4450   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.8301   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -0.7227   -1.2584 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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 20 25  1  0
 25 26  2  0
  5 27  1  0
 27 28  1  0
 28  2  1  0
 26  9  1  0
 15 10  1  0
 26 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 18 46  1  0
 19 47  1  0
 25 48  1  0
 27 49  1  0
 27 50  1  0
 28 51  1  0
 28 52  1  0
M  END

831
  Mrv0541 02231215022D          

 28 31  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 28  1  0  0  0  0
  4 28  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  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 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 25  2  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014969

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3

> <INCHI_KEY>
ZEWQUBUPAILYHI-UHFFFAOYSA-N

> <FORMULA>
C21H24F3N3S

> <MOLECULAR_WEIGHT>
407.496

> <EXACT_MASS>
407.164303088

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.94441396365014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
4.655923626666667

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.389157008062217

> <JCHEM_POLAR_SURFACE_AREA>
9.72

> <JCHEM_REFRACTIVITY>
110.97530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifluoperazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014969
     RDKit          3D
Trifluoperazine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0789    0.4002   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.0417   -0.3270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.9817    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -0.3102    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.0260    0.7880 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.9871    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -0.8014    1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -0.5618   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0545   -0.5124   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.7579    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -2.9316    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013   -4.1476    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169   -4.2306    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -3.0653    1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -1.8645    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9527   -0.4389    0.8320 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714    0.8988    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    2.0472   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560    3.1120   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    2.9674   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    4.0983   -1.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172    3.7156   -3.1158 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    5.1809   -1.9471 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902    4.5112   -1.1104 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258    1.7873   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    0.6985   -0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.3772   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352    0.3554   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    1.1306   -0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.0525    0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -0.4464   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.8386    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.9017    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -0.4582    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -1.1313    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.9966    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.1585    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.5043    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.2069    1.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    0.4534   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -1.3114   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -2.8716   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -5.0502    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1550   -5.1802    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4913   -3.1298    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389    2.0939    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7096    4.0349   -1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.8103   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428   -0.3219   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    1.4450   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.8301   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -0.7227   -1.2584 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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 20 25  1  0
 25 26  2  0
  5 27  1  0
 27 28  1  0
 28  2  1  0
 26  9  1  0
 15 10  1  0
 26 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 18 46  1  0
 19 47  1  0
 25 48  1  0
 27 49  1  0
 27 50  1  0
 28 51  1  0
 28 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 831                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.747  -4.978   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0      14.408  -0.530   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0      15.958  -3.191   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0      16.513  -1.086   0.000  0.00  0.00           F+0
HETATM    5  N   UNK     0       7.080   2.721   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.413   4.261   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.747  -1.898   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.080   4.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.951   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414   1.951   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   5.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413   2.721   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.414   0.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.747  -0.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   5.031   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.081  -2.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414  -2.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.081  -4.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.414  -4.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.457  -1.845   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.037  -1.845   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.852  -2.636   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.457  -5.031   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.037  -5.031   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.852  -4.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.642  -2.636   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.642  -4.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.183  -1.861   0.000  0.00  0.00           C+0
CONECT    1   18   19                                                       
CONECT    2   28                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    8    9   10                                                  
CONECT    6   11   12   15                                                  
CONECT    7   14   16   17                                                  
CONECT    8    5   11                                                       
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    6    8                                                       
CONECT   12    6    9                                                       
CONECT   13   10   14                                                       
CONECT   14    7   13                                                       
CONECT   15    6                                                            
CONECT   16    7   18   20                                                  
CONECT   17    7   19   21                                                  
CONECT   18    1   16   23                                                  
CONECT   19    1   17   24                                                  
CONECT   20   16   22                                                       
CONECT   21   17   26                                                       
CONECT   22   20   25   28                                                  
CONECT   23   18   25                                                       
CONECT   24   19   27                                                       
CONECT   25   22   23                                                       
CONECT   26   21   27                                                       
CONECT   27   24   26                                                       
CONECT   28    2    3    4   22                                             
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014969
HETATM    1  C1  UNL     1       6.079   0.400  -0.544  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.761   1.042  -0.327  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.463   0.982   1.100  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.674  -0.310   1.324  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.327   0.026   0.788  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.421  -0.987   1.172  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.008  -0.801   1.052  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.560  -0.562  -0.337  1.00  0.00           C  
HETATM    9  N3  UNL     1      -2.054  -0.512  -0.172  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.602  -1.758   0.282  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.828  -2.932   0.222  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.401  -4.148   0.559  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.717  -4.231   0.952  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.447  -3.065   1.000  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.914  -1.864   0.678  1.00  0.00           C  
HETATM   16  S1  UNL     1      -4.953  -0.439   0.832  1.00  0.00           S  
HETATM   17  C13 UNL     1      -4.071   0.899   0.024  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.781   2.047  -0.215  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.156   3.112  -0.815  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.816   2.967  -1.155  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.101   4.098  -1.831  1.00  0.00           C  
HETATM   22  F1  UNL     1      -1.717   3.716  -3.116  1.00  0.00           F  
HETATM   23  F2  UNL     1      -2.929   5.181  -1.947  1.00  0.00           F  
HETATM   24  F3  UNL     1      -0.990   4.511  -1.110  1.00  0.00           F  
HETATM   25  C18 UNL     1      -2.126   1.787  -0.899  1.00  0.00           C  
HETATM   26  C19 UNL     1      -2.751   0.699  -0.289  1.00  0.00           C  
HETATM   27  C20 UNL     1       2.435   0.377  -0.595  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.835   0.355  -1.152  1.00  0.00           C  
HETATM   29  H1  UNL     1       6.793   1.131  -0.913  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.373  -0.052   0.428  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.999  -0.446  -1.269  1.00  0.00           H  
HETATM   32  H4  UNL     1       3.863   1.839   1.445  1.00  0.00           H  
HETATM   33  H5  UNL     1       5.391   0.902   1.664  1.00  0.00           H  
HETATM   34  H6  UNL     1       3.509  -0.458   2.404  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.106  -1.131   0.771  1.00  0.00           H  
HETATM   36  H8  UNL     1       1.738  -1.997   0.772  1.00  0.00           H  
HETATM   37  H9  UNL     1       1.614  -1.158   2.304  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.626  -1.504   1.662  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.275   0.207   1.598  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.225   0.453  -0.593  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.283  -1.311  -1.082  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.806  -2.872  -0.120  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.782  -5.050   0.505  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.155  -5.180   1.215  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.491  -3.130   1.307  1.00  0.00           H  
HETATM   46  H18 UNL     1      -5.839   2.094   0.079  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.710   4.035  -1.008  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.097   1.810  -1.227  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.843  -0.322  -1.257  1.00  0.00           H  
HETATM   50  H22 UNL     1       2.079   1.445  -0.733  1.00  0.00           H  
HETATM   51  H23 UNL     1       3.763   0.830  -2.174  1.00  0.00           H  
HETATM   52  H24 UNL     1       4.146  -0.723  -1.258  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   28
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   27
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   26
CONECT   10   11   11   15
CONECT   11   12   42
CONECT   12   13   13   43
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   26
CONECT   18   19   46
CONECT   19   20   20   47
CONECT   20   21   25
CONECT   21   22   23   24
CONECT   25   26   26   48
CONECT   27   28   49   50
CONECT   28   51   52
END

HMDB0014969
     RDKit          3D
Trifluoperazine
 52 55  0  0  0  0  0  0  0  0999 V2000
    6.0789    0.4002   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    1.0417   -0.3270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.9817    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -0.3102    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.0260    0.7880 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.9871    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -0.8014    1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -0.5618   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0545   -0.5124   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.7579    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -2.9316    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013   -4.1476    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169   -4.2306    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -3.0653    1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -1.8645    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9527   -0.4389    0.8320 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714    0.8988    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    2.0472   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560    3.1120   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    2.9674   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    4.0983   -1.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172    3.7156   -3.1158 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    5.1809   -1.9471 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902    4.5112   -1.1104 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258    1.7873   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    0.6985   -0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355    0.3772   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352    0.3554   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    1.1306   -0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.0525    0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -0.4464   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.8386    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.9017    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -0.4582    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -1.1313    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.9966    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.1585    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.5043    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.2069    1.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    0.4534   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -1.3114   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -2.8716   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -5.0502    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1550   -5.1802    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4913   -3.1298    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8389    2.0939    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7096    4.0349   -1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.8103   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428   -0.3219   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    1.4450   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.8301   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -0.7227   -1.2584 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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 20 25  1  0
 25 26  2  0
  5 27  1  0
 27 28  1  0
 28  2  1  0
 26  9  1  0
 15 10  1  0
 26 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 18 46  1  0
 19 47  1  0
 25 48  1  0
 27 49  1  0
 27 50  1  0
 28 51  1  0
 28 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine	ChEBI
10-[3-(4-METHYL-piperazin-1-yl)-propyl]-2-trifluoromethyl-10H-phenothiazine	ChEBI
Trifluoperazina	ChEBI
Trifluoperazinum	ChEBI
Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine	ChEBI
Trifluoroperazine	ChEBI
Trifluperazine	ChEBI
Apo-trifluoperazine	Kegg
Trifluoperazin	HMDB
Trifluoromethylperazine	HMDB
Trifluroperizine	HMDB
Rhone poulenc rorer brand OF trifluoperazine hydrochloride	HMDB
Rhone-poulenc rorer brand OF trifluoperazine hydrochloride	HMDB
Trifluoperazine HCL	HMDB
Allphar brand OF trifluoperazine hydrochloride	HMDB
Apotex brand OF trifluoperazine hydrochloride	HMDB
GlaxoSmithKline brand OF trifluoperazine hydrochloride	HMDB
Link brand OF trifluoperazine hydrochloride	HMDB
Psicofarma brand OF trifluoperazine hydrochloride	HMDB
SmithKline beecham brand OF trifluoperazine hydrochloride	HMDB
Stelazine	HMDB
Triftazin	HMDB
Apo trifluoperazine	HMDB
ApoTrifluoperazine	HMDB
Eskazine	HMDB
Flupazine	HMDB
Scios brand OF trifluoperazine hydrochloride	HMDB
Terfluzine	HMDB
Trifluoperazine hydrochloride	HMDB

Chemical Formula

C₂₁H₂₄F₃N₃S

Average Molecular Weight

407.496

Monoisotopic Molecular Weight

407.164303088

IUPAC Name

10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

Traditional Name

trifluoperazine

CAS Registry Number

117-89-5

SMILES

CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

InChI Identifier

InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3

InChI Key

ZEWQUBUPAILYHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
N-alkylpiperazine
N-methylpiperazine
Para-thiazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Amine
Alkyl halide
Alkyl fluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:45951 )
organofluorine compound (CHEBI:45951 )
N-alkylpiperazine (CHEBI:45951 )
N-methylpiperazine (CHEBI:45951 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014969)
Membrane (HMDB: HMDB0014969)

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	0.0088 g/L	Not Available
LogP	4.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	188.1	30932474
[M+H]+	Not Available	188.459	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000977

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0088 g/L	ALOGPS
logP	4.87	ALOGPS
logP	4.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.98 m³·mol⁻¹	ChemAxon
Polarizability	41.94 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]+	194.64	30932474
DeepCCS	[M-H]-	192.14	30932474
DeepCCS	[M-2H]-	226.574	30932474
DeepCCS	[M+Na]+	202.059	30932474
AllCCS	[M+H]+	194.1	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	196.3	32859911
AllCCS	[M+Na]+	196.9	32859911
AllCCS	[M-H]-	189.5	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	188.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trifluoperazine	CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	3663.3	Standard polar	33892256
Trifluoperazine	CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	2707.5	Standard non polar	33892256
Trifluoperazine	CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	2657.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine EI-B (Non-derivatized)	splash10-03kc-9730000000-49438d7f5a4236b51602	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine EI-B (Non-derivatized)	splash10-08mi-8921200000-2aff2d698385cab14cdb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine CI-B (Non-derivatized)	splash10-0002-9000100000-e2406a8adccd141c03e7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine EI-B (Non-derivatized)	splash10-03kc-9730000000-49438d7f5a4236b51602	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine EI-B (Non-derivatized)	splash10-08mi-8921200000-2aff2d698385cab14cdb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trifluoperazine CI-B (Non-derivatized)	splash10-0002-9000100000-e2406a8adccd141c03e7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifluoperazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0irv-9667000000-deccae3c053209941ea9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifluoperazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9740000000-e505b8906d154e2285a4	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-QQ , positive-QTOF	splash10-0a4i-0000900000-a01e8dfa304983005945	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-QQ , positive-QTOF	splash10-0a4i-0000900000-7b23271ee0eec105a7c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-QQ , positive-QTOF	splash10-06r6-0900500000-0ea8c080e1d078157f50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-QQ , positive-QTOF	splash10-03dl-1900000000-2608f082c54c542054e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-QQ , positive-QTOF	splash10-0229-8910000000-5b36d7157269ff6ba38c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine LC-ESI-IT , positive-QTOF	splash10-0006-0901000000-06a3d20c96b187c19fad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine , positive-QTOF	splash10-0a4i-0110900000-8af3aa3c7acbf89b8b20	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trifluoperazine 35V, Positive-QTOF	splash10-0btc-1911400000-46dc3c49b2371e4bfb02	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 10V, Positive-QTOF	splash10-0a4i-0102900000-c7f3c26a540bba469a6d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 20V, Positive-QTOF	splash10-0a4l-3918600000-0425f149418e81474ddd	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 40V, Positive-QTOF	splash10-0a4i-9623000000-d1310936305ee7ea664e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 10V, Negative-QTOF	splash10-0a4i-0001900000-ce43ff55b11825ac5096	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 20V, Negative-QTOF	splash10-052b-0090200000-5c65bf0b372d774d4385	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 40V, Negative-QTOF	splash10-014i-4390000000-7c7e77cb89eafbe85363	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 10V, Positive-QTOF	splash10-0a4i-0000900000-100cfe5f7d72e7cb4519	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 20V, Positive-QTOF	splash10-0a4l-0901800000-10b4b4fb7a8c235ad902	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 40V, Positive-QTOF	splash10-0c0r-9612100000-f822b67e0486f6cde009	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 10V, Negative-QTOF	splash10-0a4i-0000900000-93423d8802c27fe68345	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 20V, Negative-QTOF	splash10-0a4i-0026900000-7f5cdc5d710c6a312dc8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluoperazine 40V, Negative-QTOF	splash10-014i-0193000000-421df1fba238d9cd5da6	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00831	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00831	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

DB00831

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5365

KEGG Compound ID

C07168

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trifluoperazine

METLIN ID

Not Available

PubChem Compound

5566

PDB ID

TFP

ChEBI ID

45951

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. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

References

Hirata Y, Ishii K, Taguchi T, Suita S, Takeshige K: Conversion of xanthine dehydrogenase to xanthine oxidase during ischemia of the rat small intestine and the effect of trifluoperazine on the conversion. J Pediatr Surg. 1993 Apr;28(4):597-600. [PubMed:8483075 ]
Greene EL, Paller MS: Calcium and free radicals in hypoxia/reoxygenation injury of renal epithelial cells. Am J Physiol. 1994 Jan;266(1 Pt 2):F13-20. [PubMed:8304479 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

References

Kerdpin O, Mackenzie PI, Bowalgaha K, Finel M, Miners JO: Influence of N-terminal domain histidine and proline residues on the substrate selectivities of human UDP-glucuronosyltransferase 1A1, 1A6, 1A9, 2B7, and 2B10. Drug Metab Dispos. 2009 Sep;37(9):1948-55. doi: 10.1124/dmd.109.028225. Epub 2009 Jun 1. [PubMed:19487247 ]
Fujiwara R, Nakajima M, Yamanaka H, Katoh M, Yokoi T: Interactions between human UGT1A1, UGT1A4, and UGT1A6 affect their enzymatic activities. Drug Metab Dispos. 2007 Oct;35(10):1781-7. Epub 2007 Jul 9. [PubMed:17620344 ]
Uchaipichat V, Mackenzie PI, Elliot DJ, Miners JO: Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases. Drug Metab Dispos. 2006 Mar;34(3):449-56. Epub 2005 Dec 28. [PubMed:16381668 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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

4. 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 ]
Lahti RA, Evans DL, Stratman NC, Figur LM: Dopamine D4 versus D2 receptor selectivity of dopamine receptor antagonists: possible therapeutic implications. Eur J Pharmacol. 1993 Jun 4;236(3):483-6. [PubMed:8102973 ]
Schmidt MH, Lee T: Investigation of striatal dopamine D2 receptor acquisition following prenatal neuroleptic exposure. Psychiatry Res. 1991 Mar;36(3):319-28. [PubMed:1676523 ]
Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]
Seeman P, Lee T, Chau-Wong M, Wong K: Antipsychotic drug doses and neuroleptic/dopamine receptors. Nature. 1976 Jun 24;261(5562):717-9. [PubMed:945467 ]

Enzyme Details

5. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Torres-Piedra M, Figueroa M, Hernandez-Abreu O, Ibarra-Barajas M, Navarrete-Vazquez G, Estrada-Soto S: Vasorelaxant effect of flavonoids through calmodulin inhibition: Ex vivo, in vitro, and in silico approaches. Bioorg Med Chem. 2011 Jan 1;19(1):542-6. doi: 10.1016/j.bmc.2010.10.063. Epub 2010 Nov 4. [PubMed:21129983 ]

Enzyme Details

6. 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 ]
Fujinaga M, Hoffman BB, Baden JM: Receptor subtype and intracellular signal transduction pathway associated with situs inversus induced by alpha 1 adrenergic stimulation in rat embryos. Dev Biol. 1994 Apr;162(2):558-67. [PubMed:8150214 ]
Huerta-Bahena J, Villalobos-Molina R, Garcia-Sainz JA: Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects. Mol Pharmacol. 1983 Jan;23(1):67-70. [PubMed:6135146 ]

Enzyme Details

7. Neuron-specific vesicular protein calcyon

General function:: Involved in dopamine receptor binding
Specific function:: Interacts with clathrin light chain A and stimulates clathrin self-assembly and clathrin-mediated endocytosis
Gene Name:: CALY
Uniprot ID:: Q9NYX4
Molecular weight:: 23433.5

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, Lee T, Chau-Wong M, Wong K: Antipsychotic drug doses and neuroleptic/dopamine receptors. Nature. 1976 Jun 24;261(5562):717-9. [PubMed:945467 ]
Madrid PB, Polgar WE, Toll L, Tanga MJ: Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors. Bioorg Med Chem Lett. 2007 Jun 1;17(11):3014-7. Epub 2007 Mar 24. [PubMed:17407813 ]

Enzyme Details

8. Protein S100-A4

General function:: Involved in calcium ion binding
Specific function:: Not Available
Gene Name:: S100A4
Uniprot ID:: P26447
Molecular weight:: 11728.4

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Malashkevich VN, Dulyaninova NG, Ramagopal UA, Liriano MA, Varney KM, Knight D, Brenowitz M, Weber DJ, Almo SC, Bresnick AR: Phenothiazines inhibit S100A4 function by inducing protein oligomerization. Proc Natl Acad Sci U S A. 2010 May 11;107(19):8605-10. doi: 10.1073/pnas.0913660107. Epub 2010 Apr 26. [PubMed:20421509 ]

Enzyme Details

9. Troponin C, slow skeletal and cardiac muscles

General function:: Involved in calcium ion binding
Specific function:: Troponin is the central regulatory protein of striated muscle contraction. Tn consists of three components:Tn-I which is the inhibitor of actomyosin ATPase, Tn-T which contains the binding site for tropomyosin and Tn-C. The binding of calcium to Tn-C abolishes the inhibitory action of Tn on actin filaments
Gene Name:: TNNC1
Uniprot ID:: P63316
Molecular weight:: 18402.4

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kleerekoper Q, Liu W, Choi D, Putkey JA: Identification of binding sites for bepridil and trifluoperazine on cardiac troponin C. J Biol Chem. 1998 Apr 3;273(14):8153-60. [PubMed:9525919 ]

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

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]

Showing metabocard for Trifluoperazine (HMDB0014969)

MOL for HMDB0014969 (Trifluoperazine)

3D MOL for HMDB0014969 (Trifluoperazine)

3D SDF for HMDB0014969 (Trifluoperazine)

3D-SDF for HMDB0014969 (Trifluoperazine)

PDB for HMDB0014969 (Trifluoperazine)

3D PDB for HMDB0014969 (Trifluoperazine)

SMILES for HMDB0014969 (Trifluoperazine)

INCHI for HMDB0014969 (Trifluoperazine)

Structure for HMDB0014969 (Trifluoperazine)

3D Structure for HMDB0014969 (Trifluoperazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

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