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

ID: ALA1710

Cas Number: 1250-26-6

PubChem CID: 2913535

Max Phase: Preclinical

Molecular Formula: C21H25ClF3N3S

Molecular Weight: 407.51

Molecule Type: Small molecule

Names and Identifiers

Trade Names(2): Stelazine | Trifluoperazine HCl

Canonical SMILES:  CN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1.Cl

Standard InChI:  InChI=1S/C21H24F3N3S.ClH/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;1H

Standard InChI Key:  RIULCFSTKRDHBX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.0536    3.3604    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965    1.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    5.9832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468    7.4587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1973    2.7005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2356    0.9002    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360    2.1000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120    3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9549    8.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489    7.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266    5.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3293    5.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    8.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  8  1  0
  5 10  1  0
  6  3  1  0
  7  2  1  0
  8  7  2  0
  9  3  2  0
 10  9  1  0
 11 24  1  0
 12 20  1  0
 13  6  2  0
 14 10  2  0
 15  5  1  0
 16  5  1  0
 17  5  1  0
 18  2  1  0
 19 21  1  0
 20 22  1  0
 21 11  1  0
 22 11  1  0
 23 18  1  0
 24 23  1  0
 25  7  1  0
 26  8  1  0
 27 12  1  0
 28 25  2  0
 29 28  1  0
  6  4  1  0
 26 29  2  0
 13 14  1  0
 19 12  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 407.51

Molecular Weight (Monoisotopic): 407.1643

AlogP: 4.95

#Rotatable Bonds: 4

Polar Surface Area: 9.72

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.99

CX LogP: 4.66

CX LogD: 3.97

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.51

References

1. Madrid PB, Polgar WE, Toll L, Tanga MJ..  (2007)  Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors.,  17  (11): [PMID:17407813] [10.1016/j.bmcl.2007.03.064]

2. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

15. PubChem BioAssay data set, 

16. Kato Y, Nakajima M, Oda S, Fukami T, Yokoi T..  (2012)  Human UDP-glucuronosyltransferase isoforms involved in haloperidol glucuronidation and quantitative estimation of their contribution.,  40  (2): [PMID:22028316] [10.1124/dmd.111.042150]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays