4-[3-(4-Chloro-phenyl)-3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl]-1-(4-fluoro-phenyl)-butan-1-one

ID: ALA210578

Chembl Id: CHEMBL210578

PubChem CID: 13091268

Max Phase: Preclinical

Molecular Formula: C23H25ClFNO2

Molecular Weight: 401.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCN1C2CCC1CC(O)(c1ccc(Cl)cc1)C2)c1ccc(F)cc1

Standard InChI:  InChI=1S/C23H25ClFNO2/c24-18-7-5-17(6-8-18)23(28)14-20-11-12-21(15-23)26(20)13-1-2-22(27)16-3-9-19(25)10-4-16/h3-10,20-21,28H,1-2,11-15H2

Standard InChI Key:  CXQUOFVDYCOSEZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA210578

   4-[3-(4-Chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]-1-(4-fluorophenyl)butan-1-one

2. Alternative Forms:

   

   ALA210578

   4-[3-(4-Chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-1-(4-fluorophenyl)butan-1-one;hydrochloride

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: 401.91

Molecular Weight (Monoisotopic): 401.1558

AlogP: 4.96

#Rotatable Bonds: 6

Polar Surface Area: 40.54

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.95

CX Basic pKa: 8.65

CX LogP: 4.19

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: -0.71

References

1. Sikazwe DM, Li S, Lyles-Eggleston M, Ablordeppey SY..  (2003)  The acute EPS of haloperidol may be unrelated to its metabolic transformation to BCPP+.,  13  (21): [PMID:14552778] [10.1016/j.bmcl.2003.07.015]

2. Ablordeppey SY, Lyles-Eggleston M, Bricker B, Zhang W, Zhu X, Goodman C, Roth BL..  (2006)  Evaluation of the eutomer of 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, {(+)-SYA 09}, a pyrrolidine analog of haloperidol.,  16  (12): [PMID:16621538] [10.1016/j.bmcl.2006.03.057]

3. Ablordeppey SY, Altundas R, Bricker B, Zhu XY, Kumar EV, Jackson T, Khan A, Roth BL..  (2008)  Identification of a butyrophenone analog as a potential atypical antipsychotic agent: 4-[4-(4-chlorophenyl)-1,4-diazepan-1-yl]-1-(4-fluorophenyl)butan-1-one.,  16  (15): [PMID:18595716] [10.1016/j.bmc.2008.06.030]

4. Sikazwe DM, Nkansah NT, Altundas R, Zhu XY, Roth BL, Setola V, Ablordeppey SY..  (2009)  Synthesis and evaluation of ligands for D2-like receptors: the role of common pharmacophoric groups.,  17  (4): [PMID:19155177] [10.1016/j.bmc.2008.12.054]

5. Sampson D, Bricker B, Zhu XY, Peprah K, Lamango NS, Setola V, Roth BL, Ablordeppey SY..  (2014)  Further evaluation of the tropane analogs of haloperidol.,  24  (17): [PMID:25070422] [10.1016/j.bmcl.2014.07.018]

6. Etukala JR, Zhu XY, Eyunni SV, Onyameh EK, Ofori E, Bricker BA, Kang HJ, Huang XP, Roth BL, Ablordeppey SY..  (2016)  Development of CNS multi-receptor ligands: Modification of known D2 pharmacophores.,  24  (16): [PMID:27364609] [10.1016/j.bmc.2016.06.011]

Source

Source(1):

• Scientific Literature