ID: ALA385587

Max Phase: Preclinical

Molecular Formula: C21H24ClN3O5S

Molecular Weight: 465.96

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O

Standard InChI:  InChI=1S/C21H24ClN3O5S/c1-14(20(26)24-8-10-30-11-9-24)25-7-6-19(21(25)27)23-31(28,29)18-5-3-15-12-17(22)4-2-16(15)13-18/h2-5,12-14,19,23H,6-11H2,1H3/t14-,19-/m0/s1

Standard InChI Key:  ICLOZQFWTRAYPX-LIRRHRJNSA-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: 465.96

Molecular Weight (Monoisotopic): 465.1125

AlogP: 1.62

#Rotatable Bonds: 5

Polar Surface Area: 96.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.04

CX Basic pKa:

CX LogP: 1.08

CX LogD: 1.08

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.72

Np Likeness Score: -1.58

References

1. Watson NS, Brown D, Campbell M, Chan C, Chaudry L, Convery MA, Fenwick R, Hamblin JN, Haslam C, Kelly HA, King NP, Kurtis CL, Leach AR, Manchee GR, Mason AM, Mitchell C, Patel C, Patel VK, Senger S, Shah GP, Weston HE, Whitworth C, Young RJ..  (2006)  Design and synthesis of orally active pyrrolidin-2-one-based factor Xa inhibitors.,  16  (14): [PMID:16697194] [10.1016/j.bmcl.2006.04.053]

2. Young RJ, Campbell M, Borthwick AD, Brown D, Burns-Kurtis CL, Chan C, Convery MA, Crowe MC, Dayal S, Diallo H, Kelly HA, King NP, Kleanthous S, Mason AM, Mordaunt JE, Patel C, Pateman AJ, Senger S, Shah GP, Smith PW, Watson NS, Weston HE, Zhou P..  (2006)  Structure- and property-based design of factor Xa inhibitors: pyrrolidin-2-ones with acyclic alanyl amides as P4 motifs.,  16  (23): [PMID:16982190] [10.1016/j.bmcl.2006.09.001]

3. Chan C, Borthwick AD, Brown D, Burns-Kurtis CL, Campbell M, Chaudry L, Chung CW, Convery MA, Hamblin JN, Johnstone L, Kelly HA, Kleanthous S, Patikis A, Patel C, Pateman AJ, Senger S, Shah GP, Toomey JR, Watson NS, Weston HE, Whitworth C, Young RJ, Zhou P..  (2007)  Factor Xa inhibitors: S1 binding interactions of a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides.,  50  (7): [PMID:17338508] [10.1021/jm060870c]

4. Pinto DJ, Smallheer JM, Cheney DL, Knabb RM, Wexler RR..  (2010)  Factor Xa inhibitors: next-generation antithrombotic agents.,  53  (17): [PMID:20503967] [10.1021/jm100146h]

Source

Source(1):

• Scientific Literature