Jump To Section:

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 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014761

Secondary Accession Numbers

HMDB14761

Metabolite Identification

Common Name

Fluphenazine

Description

Fluphenazine is only found in individuals that have used or taken this drug. It is a phenothiazine used in the treatment of psychoses. Its properties and uses are generally similar to those of chlorpromazine. [PubChem]Fluphenazine 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

623
  Mrv0541 02231214492D          

 30 33  0  0  0  0            999 V2000
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4328   -1.1584    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631   -2.5840    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5608   -1.4561    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8480   -1.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 30  1  0  0  0  0
  3 30  1  0  0  0  0
  4 30  1  0  0  0  0
  5 17  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 20  2  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 27  1  0  0  0  0
 24 30  1  0  0  0  0
 25 27  2  0  0  0  0
 26 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

HMDB0014761
     RDKit          3D
Fluphenazine
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.8462   -1.0677   -1.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0442    0.1437   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9719    0.3468    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    0.4273   -0.3466 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.7936   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -1.1990   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.1337   -0.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.6301   -0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037    0.3050    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822    0.1488    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325    0.4189    0.2690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232    1.8460    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    2.7586    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    4.1331    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    4.6030   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770    3.6983   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769    2.3438   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.3071   -1.4695 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7925   -0.3453   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7054   -1.3145   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713   -2.6128   -0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -2.9073   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0776   -4.3084    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -4.6299    1.3706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -4.6255    0.4730 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617   -5.1449   -0.7431 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -1.9106    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.5577   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848    0.6528    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    0.9509    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -1.8336   -0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0229    0.0802   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870    0.9774   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -0.4475    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083    1.3167    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6897   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561   -0.7746   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.6574   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986   -2.0553   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.6063    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.7383   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361    1.2984   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.6973    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.9293    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651    0.7069    2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    2.4443    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451    4.8194    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    5.6912   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0488    4.0914   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5941   -1.0381   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1735   -3.4271   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606   -2.2128    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.0808    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759    1.6276    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908    2.0525    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779    0.6229    1.7037 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  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 27 28  2  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
 10 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 30 56  1  0
M  END

623
  Mrv0541 02231214492D          

 30 33  0  0  0  0            999 V2000
    5.9361   -3.5410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4328   -1.1584    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631   -2.5840    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5608   -1.4561    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843   -3.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1352   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -3.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8480   -1.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 30  1  0  0  0  0
  3 30  1  0  0  0  0
  4 30  1  0  0  0  0
  5 17  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 20  2  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 27  1  0  0  0  0
 24 30  1  0  0  0  0
 25 27  2  0  0  0  0
 26 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014761

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2

> <INCHI_KEY>
PLDUPXSUYLZYBN-UHFFFAOYSA-N

> <FORMULA>
C22H26F3N3OS

> <MOLECULAR_WEIGHT>
437.522

> <EXACT_MASS>
437.174867774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.91856262387888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
3.965821614666666

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.593098118537455

> <JCHEM_PKA_STRONGEST_BASIC>
8.211427951218774

> <JCHEM_POLAR_SURFACE_AREA>
29.950000000000003

> <JCHEM_REFRACTIVITY>
117.26760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluphenazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014761
     RDKit          3D
Fluphenazine
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.8462   -1.0677   -1.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0442    0.1437   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9719    0.3468    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    0.4273   -0.3466 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.7936   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -1.1990   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.1337   -0.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.6301   -0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037    0.3050    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822    0.1488    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325    0.4189    0.2690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232    1.8460    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    2.7586    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    4.1331    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    4.6030   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770    3.6983   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769    2.3438   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.3071   -1.4695 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7925   -0.3453   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7054   -1.3145   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713   -2.6128   -0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -2.9073   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0776   -4.3084    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -4.6299    1.3706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -4.6255    0.4730 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617   -5.1449   -0.7431 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -1.9106    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.5577   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848    0.6528    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    0.9509    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -1.8336   -0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0229    0.0802   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870    0.9774   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -0.4475    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083    1.3167    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6897   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561   -0.7746   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.6574   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986   -2.0553   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.6063    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.7383   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361    1.2984   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.6973    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.9293    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651    0.7069    2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    2.4443    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451    4.8194    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    5.6912   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0488    4.0914   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5941   -1.0381   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1735   -3.4271   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606   -2.2128    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.0808    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759    1.6276    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908    2.0525    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779    0.6229    1.7037 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  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 27 28  2  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
 10 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 30 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 623                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.081  -6.610   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0      15.741  -2.162   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0      17.291  -4.823   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0      17.847  -2.718   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       3.080   5.708   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.414   1.089   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.747   2.629   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.081  -3.530   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.080   0.319   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414   2.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.080   3.399   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.747   0.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.747  -1.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413   3.399   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.081  -1.991   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.413   4.938   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.414  -4.300   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.747  -4.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.414  -5.840   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.747  -5.840   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.791  -3.477   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.371  -3.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.186  -4.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.791  -6.663   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.371  -6.663   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.186  -5.872   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.975  -4.268   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.975  -5.872   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.516  -3.493   0.000  0.00  0.00           C+0
CONECT    1   20   21                                                       
CONECT    2   30                                                            
CONECT    3   30                                                            
CONECT    4   30                                                            
CONECT    5   17                                                            
CONECT    6    9   10   13                                                  
CONECT    7   11   12   15                                                  
CONECT    8   16   18   19                                                  
CONECT    9    6   11                                                       
CONECT   10    6   12                                                       
CONECT   11    7    9                                                       
CONECT   12    7   10                                                       
CONECT   13    6   14                                                       
CONECT   14   13   16                                                       
CONECT   15    7   17                                                       
CONECT   16    8   14                                                       
CONECT   17    5   15                                                       
CONECT   18    8   20   22                                                  
CONECT   19    8   21   23                                                  
CONECT   20    1   18   25                                                  
CONECT   21    1   19   26                                                  
CONECT   22   18   24                                                       
CONECT   23   19   28                                                       
CONECT   24   22   27   30                                                  
CONECT   25   20   27                                                       
CONECT   26   21   29                                                       
CONECT   27   24   25                                                       
CONECT   28   23   29                                                       
CONECT   29   26   28                                                       
CONECT   30    2    3    4   24                                             
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0014761
HETATM    1  O1  UNL     1       6.846  -1.068  -1.482  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.044   0.144  -0.807  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.972   0.347   0.189  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.630   0.427  -0.347  1.00  0.00           N  
HETATM    5  C3  UNL     1       4.210  -0.794  -0.900  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.763  -1.199  -0.771  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.916  -0.134  -0.416  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.543  -0.630  -0.228  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.204   0.305   0.644  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.582   0.149   1.084  1.00  0.00           C  
HETATM   11  N3  UNL     1      -2.733   0.419   0.269  1.00  0.00           N  
HETATM   12  C8  UNL     1      -2.923   1.846   0.033  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.028   2.759   0.611  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.246   4.133   0.457  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.324   4.603  -0.250  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.177   3.698  -0.802  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.977   2.344  -0.661  1.00  0.00           C  
HETATM   18  S1  UNL     1      -5.161   1.307  -1.469  1.00  0.00           S  
HETATM   19  C14 UNL     1      -4.792  -0.345  -0.914  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.705  -1.314  -1.268  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.471  -2.613  -0.893  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.333  -2.907  -0.175  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.078  -4.308   0.263  1.00  0.00           C  
HETATM   24  F1  UNL     1      -4.840  -4.630   1.371  1.00  0.00           F  
HETATM   25  F2  UNL     1      -2.795  -4.625   0.473  1.00  0.00           F  
HETATM   26  F3  UNL     1      -4.562  -5.145  -0.743  1.00  0.00           F  
HETATM   27  C19 UNL     1      -3.437  -1.911   0.159  1.00  0.00           C  
HETATM   28  C20 UNL     1      -3.652  -0.558  -0.209  1.00  0.00           C  
HETATM   29  C21 UNL     1       2.385   0.653   0.647  1.00  0.00           C  
HETATM   30  C22 UNL     1       3.819   0.951   0.726  1.00  0.00           C  
HETATM   31  H1  UNL     1       7.152  -1.834  -0.988  1.00  0.00           H  
HETATM   32  H2  UNL     1       8.023   0.080  -0.252  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.087   0.977  -1.506  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.988  -0.448   0.974  1.00  0.00           H  
HETATM   35  H5  UNL     1       6.108   1.317   0.736  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.806  -1.690  -0.539  1.00  0.00           H  
HETATM   37  H7  UNL     1       4.456  -0.775  -2.008  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.439  -1.657  -1.769  1.00  0.00           H  
HETATM   39  H9  UNL     1       2.699  -2.055  -0.030  1.00  0.00           H  
HETATM   40  H10 UNL     1       0.589  -1.606   0.277  1.00  0.00           H  
HETATM   41  H11 UNL     1       0.104  -0.738  -1.218  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.136   1.298  -0.039  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.382   0.697   1.518  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.624  -0.929   1.510  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.765   0.707   2.082  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.212   2.444   1.233  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.545   4.819   0.898  1.00  0.00           H  
HETATM   48  H18 UNL     1      -3.467   5.691  -0.352  1.00  0.00           H  
HETATM   49  H19 UNL     1      -5.049   4.091  -1.352  1.00  0.00           H  
HETATM   50  H20 UNL     1      -6.594  -1.038  -1.833  1.00  0.00           H  
HETATM   51  H21 UNL     1      -6.173  -3.427  -1.138  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.561  -2.213   0.671  1.00  0.00           H  
HETATM   53  H23 UNL     1       2.140   0.081   1.605  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.776   1.628   0.610  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.991   2.053   0.700  1.00  0.00           H  
HETATM   56  H26 UNL     1       4.278   0.623   1.704  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   44   45
CONECT   11   12   28
CONECT   12   13   13   17
CONECT   13   14   46
CONECT   14   15   15   47
CONECT   15   16   48
CONECT   16   17   17   49
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   28
CONECT   20   21   50
CONECT   21   22   22   51
CONECT   22   23   27
CONECT   23   24   25   26
CONECT   27   28   28   52
CONECT   29   30   53   54
CONECT   30   55   56
END

HMDB0014761
     RDKit          3D
Fluphenazine
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.8462   -1.0677   -1.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0442    0.1437   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9719    0.3468    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    0.4273   -0.3466 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.7936   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -1.1990   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.1337   -0.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.6301   -0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037    0.3050    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822    0.1488    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325    0.4189    0.2690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232    1.8460    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    2.7586    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    4.1331    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    4.6030   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770    3.6983   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769    2.3438   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.3071   -1.4695 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7925   -0.3453   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7054   -1.3145   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713   -2.6128   -0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -2.9073   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0776   -4.3084    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -4.6299    1.3706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -4.6255    0.4730 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617   -5.1449   -0.7431 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -1.9106    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.5577   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848    0.6528    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    0.9509    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -1.8336   -0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0229    0.0802   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870    0.9774   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -0.4475    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083    1.3167    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6897   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561   -0.7746   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.6574   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986   -2.0553   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.6063    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1035   -0.7383   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361    1.2984   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3818    0.6973    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.9293    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651    0.7069    2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    2.4443    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451    4.8194    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    5.6912   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0488    4.0914   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5941   -1.0381   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1735   -3.4271   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606   -2.2128    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.0808    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759    1.6276    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908    2.0525    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779    0.6229    1.7037 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  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 27 28  2  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
 10 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 21 51  1  0
 27 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 30 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Hydroxyethyl)-4-(3-(trifluoromethyl-10-phenothiazinyl)propyl)-piperazine	ChEBI
10-(3'-(4''-(beta-Hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazine	ChEBI
10-(3-(2-Hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazine	ChEBI
2-(4-(3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl)-1-piperazinyl)ethanol	ChEBI
2-(Trifluoromethyl)-10-(3-(1-(beta-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine	ChEBI
4-(3-(-Trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol	ChEBI
4-(3-(2-(Trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-1-piperazineethanol	ChEBI
4-(3-(2-Trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol	ChEBI
Flufenazina	ChEBI
Fluorfenazine	ChEBI
Fluorophenazine	ChEBI
Fluorphenazine	ChEBI
Fluphenazinum	ChEBI
Triflumethazine	ChEBI
Moditen	Kegg
10-(3'-(4''-(b-Hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazine	Generator
10-(3'-(4''-(Β-hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazine	Generator
2-(Trifluoromethyl)-10-(3-(1-(b-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine	Generator
2-(Trifluoromethyl)-10-(3-(1-(β-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine	Generator
Fluphenazine decanoate	HMDB
Fluphenazine hydrochloride	HMDB
Lyogen	HMDB
Prolixin	HMDB
Hydrochloride, fluphenazine	HMDB
Flufenazin	HMDB

Chemical Formula

C₂₂H₂₆F₃N₃OS

Average Molecular Weight

437.522

Monoisotopic Molecular Weight

437.174867774

IUPAC Name

2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol

Traditional Name

fluphenazine

CAS Registry Number

69-23-8

SMILES

OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

InChI Identifier

InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2

InChI Key

PLDUPXSUYLZYBN-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
Para-thiazine
1,4-diazinane
Benzenoid
Piperazine
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Alkanolamine
Azacycle
Thioether
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Amine
Alkyl halide
Alkyl fluoride
Organopnictogen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:5123 )
organofluorine compound (CHEBI:5123 )
N-alkylpiperazine (CHEBI:5123 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.019 g/L	Not Available
LogP	4.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.4	ALOGPS
logP	3.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.95 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.27 m³·mol⁻¹	ChemAxon
Polarizability	44.92 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]+	198.987	30932474
DeepCCS	[M-H]-	196.629	30932474
DeepCCS	[M-2H]-	230.71	30932474
DeepCCS	[M+Na]+	206.011	30932474
AllCCS	[M+H]+	199.2	32859911
AllCCS	[M+H-H2O]+	197.1	32859911
AllCCS	[M+NH4]+	201.1	32859911
AllCCS	[M+Na]+	201.7	32859911
AllCCS	[M-H]-	193.8	32859911
AllCCS	[M+Na-2H]-	193.7	32859911
AllCCS	[M+HCOO]-	193.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	3993.2	Standard polar	33892256
Fluphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	3079.0	Standard non polar	33892256
Fluphenazine	OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1	2988.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluphenazine,1TMS,isomer #1	C[Si](C)(C)OCCN1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(C(F)(F)F)C=C32)CC1	3096.9	Semi standard non polar	33892256
Fluphenazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN1CCN(CCCN2C3=CC=CC=C3SC3=CC=C(C(F)(F)F)C=C32)CC1	3286.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Fluphenazine EI-B (Non-derivatized)	splash10-0bu4-9430100000-8ccf208ff236ff33462c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fluphenazine EI-B (Non-derivatized)	splash10-0bu4-9430100000-8ccf208ff236ff33462c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluphenazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-5545900000-cdc372e9bc4eddfcf306	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluphenazine GC-MS (1 TMS) - 70eV, Positive	splash10-0kfx-7374900000-19e721adf0c41ac35702	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluphenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-2391100000-6928faa0b341426b2c11	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 - Fluphenazine LC-ESI-qTof , Positive-QTOF	splash10-014i-0190000000-cf20413d597a3759305d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluphenazine , positive-QTOF	splash10-000i-0310900000-a2a4be9e30f6506c9359	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluphenazine , positive-QTOF	splash10-014i-0190000000-cf20413d597a3759305d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluphenazine 35V, Positive-QTOF	splash10-007c-0911400000-e777fb408b0f7c2a2c88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluphenazine 35V, Negative-QTOF	splash10-0udi-0000900000-f3e326fb412f9c344ad9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 10V, Positive-QTOF	splash10-000i-0101900000-fb12e05240ff28e3f762	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 20V, Positive-QTOF	splash10-05g0-3714900000-faf32fabda604029301c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 40V, Positive-QTOF	splash10-0a4i-7934100000-f37950a800425ffc5ec8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 10V, Negative-QTOF	splash10-000i-0000900000-d99d8367eb6a2ea7f9a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 20V, Negative-QTOF	splash10-05r9-0198700000-1fae13d1c97088459b86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 40V, Negative-QTOF	splash10-014i-4490000000-017cae32ebc88bd742e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 10V, Positive-QTOF	splash10-000i-0000900000-1e7f5c7b20d4dd89afec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 20V, Positive-QTOF	splash10-000i-0201900000-1ca0886fa19d2ddcb4e2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 40V, Positive-QTOF	splash10-02p0-2925100000-3b2029bac39308857df0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 10V, Negative-QTOF	splash10-000i-0000900000-1cfdc24aa6524056f3c6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 20V, Negative-QTOF	splash10-052r-0001900000-1c043e72b51e2f5a44dc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluphenazine 40V, Negative-QTOF	splash10-014i-0195100000-b2cce57b45399e5b895a	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 DB00623	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00623	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

DB00623

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3255

KEGG Compound ID

C07010

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluphenazine

METLIN ID

Not Available

PubChem Compound

3372

PDB ID

Not Available

ChEBI ID

5123

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. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

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

Enzyme Details

2. Cytochrome P450 2D6

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

References

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

Enzyme Details

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

Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Hoyberg OJ, Fensbo C, Remvig J, Lingjaerde O, Sloth-Nielsen M, Salvesen I: Risperidone versus perphenazine in the treatment of chronic schizophrenic patients with acute exacerbations. Acta Psychiatr Scand. 1993 Dec;88(6):395-402. [PubMed:7508675 ]
Qin ZH, Weiss B: Dopamine receptor blockade increases dopamine D2 receptor and glutamic acid decarboxylase mRNAs in mouse substantia nigra. Eur J Pharmacol. 1994 Sep 15;269(1):25-33. [PubMed:7828655 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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

Mongin AA, Cai Z, Kimelberg HK: Volume-dependent taurine release from cultured astrocytes requires permissive [Ca(2+)](i) and calmodulin. Am J Physiol. 1999 Oct;277(4 Pt 1):C823-32. [PubMed:10516112 ]
Kawai M, Nakashima A, Ueno M, Ushimaru T, Aiba K, Doi H, Uritani M: Fission yeast tor1 functions in response to various stresses including nitrogen starvation, high osmolarity, and high temperature. Curr Genet. 2001 May;39(3):166-74. [PubMed:11409178 ]
Edlind T, Smith L, Henry K, Katiyar S, Nickels J: Antifungal activity in Saccharomyces cerevisiae is modulated by calcium signalling. Mol Microbiol. 2002 Oct;46(1):257-68. [PubMed:12366848 ]
Nakabayashi H, Komada H, Yoshida T, Takanari H, Izutsu K: Lymphocyte calmodulin and its participation in the stimulation of T lymphocytes by mitogenic lectins. Biol Cell. 1992;75(1):55-9. [PubMed:1515867 ]
Kauss H: Sensing of volume changes by poterioochromonas involves a ca-regulated system which controls activation of isofloridoside-phosphate synthase. Plant Physiol. 1981 Aug;68(2):420-4. [PubMed:16661928 ]

Enzyme Details

6. D(1A) dopamine receptor

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

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Van Kampen JM, Stoessl AJ: Dopamine D(1A) receptor function in a rodent model of tardive dyskinesia. Neuroscience. 2000;101(3):629-35. [PubMed:11113312 ]
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 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]

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 Fluphenazine (HMDB0014761)

MOL for HMDB0014761 (Fluphenazine)

3D MOL for HMDB0014761 (Fluphenazine)

3D SDF for HMDB0014761 (Fluphenazine)

3D-SDF for HMDB0014761 (Fluphenazine)

PDB for HMDB0014761 (Fluphenazine)

3D PDB for HMDB0014761 (Fluphenazine)

SMILES for HMDB0014761 (Fluphenazine)

INCHI for HMDB0014761 (Fluphenazine)

Structure for HMDB0014761 (Fluphenazine)

3D Structure for HMDB0014761 (Fluphenazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

Transporters

References