ID: ALA150161

Max Phase: Preclinical

Molecular Formula: C20H21ClFNO2

Molecular Weight: 361.84

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(CCCN1CCC(O)(c2ccc(Cl)cc2)C1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C20H21ClFNO2/c21-17-7-5-16(6-8-17)20(25)11-13-23(14-20)12-1-2-19(24)15-3-9-18(22)10-4-15/h3-10,25H,1-2,11-14H2

Standard InChI Key:  BETHXCLHMRGYBW-UHFFFAOYSA-N

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

Properties

Molecular Weight: 361.84

Molecular Weight (Monoisotopic): 361.1245

AlogP: 4.04

#Rotatable Bonds: 6

Polar Surface Area: 40.54

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.64

CX Basic pKa: 8.13

CX LogP: 3.60

CX LogD: 2.79

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.92

References

1. Lyles-Eggleston M, Altundas R, Xia J, Sikazwe DM, Fan P, Yang Q, Li S, Zhang W, Zhu X, Schmidt AW, Vanase-Frawley M, Shrihkande A, Villalobos A, Borne RF, Ablordeppey SY..  (2004)  Design, synthesis, and evaluation of metabolism-based analogues of haloperidol incapable of forming MPP+-like species.,  47  (3): [PMID:14736232] [10.1021/jm0301033]

2. Hansch C, Verma RP, Kurup A, Mekapati SB..  (2005)  The role of QSAR in dopamine interactions.,  15  (8): [PMID:15808487] [10.1016/j.bmcl.2005.02.012]

3. 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]

4. 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]

5. 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]

6. 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]

7. 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]

8. 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]

Source

Source(1):

• Scientific Literature