ID: ALA3398642

Max Phase: Preclinical

Molecular Formula: C29H25ClN8O3

Molecular Weight: 569.03

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)Nc1ccc(-c2c[nH]c([C@H](Cc3ccccc3)NC(=O)/C=C/c3cc(Cl)ccc3-n3cnnn3)n2)cc1

Standard InChI:  InChI=1S/C29H25ClN8O3/c1-41-29(40)33-23-11-7-20(8-12-23)25-17-31-28(35-25)24(15-19-5-3-2-4-6-19)34-27(39)14-9-21-16-22(30)10-13-26(21)38-18-32-36-37-38/h2-14,16-18,24H,15H2,1H3,(H,31,35)(H,33,40)(H,34,39)/b14-9+/t24-/m0/s1

Standard InChI Key:  BQHFFACTAJVDNI-WXQAMHPUSA-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: 569.03

Molecular Weight (Monoisotopic): 568.1738

AlogP: 5.00

#Rotatable Bonds: 9

Polar Surface Area: 139.71

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.50

CX Basic pKa: 5.09

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: -1.64

References

1. Pinto DJ, Smallheer JM, Corte JR, Austin EJ, Wang C, Fang T, Smith LM, Rossi KA, Rendina AR, Bozarth JM, Zhang G, Wei A, Ramamurthy V, Sheriff S, Myers JE, Morin PE, Luettgen JM, Seiffert DA, Quan ML, Wexler RR..  (2015)  Structure-based design of inhibitors of coagulation factor XIa with novel P1 moieties.,  25  (7): [PMID:25728130] [10.1016/j.bmcl.2015.01.028]

2. Corte JR, Fang T, Pinto DJ, Orwat MJ, Rendina AR, Luettgen JM, Rossi KA, Wei A, Ramamurthy V, Myers JE, Sheriff S, Narayanan R, Harper TW, Zheng JJ, Li YX, Seiffert DA, Wexler RR, Quan ML..  (2016)  Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group.,  24  (10): [PMID:27073051] [10.1016/j.bmc.2016.03.062]

Source

Source(1):

• Scientific Literature