ID: ALA1774023

Max Phase: Preclinical

Molecular Formula: C24H27Cl2N3O2

Molecular Weight: 460.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Cc1ccc(Cl)cc1)N[C@H](Cc1ccc(Cl)cc1)C(=O)N[C@H]1C[C@H]2CC[C@@H](C1)N2

Standard InChI:  InChI=1S/C24H27Cl2N3O2/c25-17-5-1-15(2-6-17)11-22(29-23(30)12-16-3-7-18(26)8-4-16)24(31)28-21-13-19-9-10-20(14-21)27-19/h1-8,19-22,27H,9-14H2,(H,28,31)(H,29,30)/t19-,20+,21+,22-/m1/s1

Standard InChI Key:  VYUFUXRLJDFDIC-CLAROIROSA-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: 460.41

Molecular Weight (Monoisotopic): 459.1480

AlogP: 3.66

#Rotatable Bonds: 7

Polar Surface Area: 70.23

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.26

CX Basic pKa: 10.98

CX LogP: 3.30

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: -0.43

References

1. Napier S, Wishart G, Arbuckle W, Baker J, Barn D, Bingham M, Brown A, Byford A, Claxton C, Craighead M, Buchanan K, Fielding L, Gibson L, Goodwin R, Goutcher S, Irving N, MacSweeney C, Milne R, Mort C, Presland J, Sloan H, Thomson F, Turnbull Z, Young T..  (2011)  The discovery of novel 8-azabicyclo[3.2.1]octan-3-yl)-3-(4-chlorophenyl) propanamides as vasopressin V1A receptor antagonists.,  21  (10): [PMID:21458261] [10.1016/j.bmcl.2011.02.096]

2. Arbuckle W, Baker J, Barn D, Bingham M, Brown A, Buchanan K, Craighead M, Goodwin R, Goutcher S, Kiczun M, Lyons A, Milne R, Montgomery B, Napier S, Presland J, Sloan H, Turnbull Z, Wishart G..  (2011)  Optimisation of pharmacokinetic properties to afford an orally bioavailable and selective V1A receptor antagonist.,  21  (15): [PMID:21700453] [10.1016/j.bmcl.2011.05.092]

Source

Source(1):

• Scientific Literature