1-(3-amino-benzo[d]isoxazol-5-yl)-6-[2'-((R)-3-hydroxy-pyrrolidin-1-ylmethyl)-biphenyl-4-yl]-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[4,3-d]pyrimidin-7-one

ID: ALA384129

PubChem CID: 23646315

Max Phase: Preclinical

Molecular Formula: C30H26F3N7O3

Molecular Weight: 589.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1noc2ccc(-n3nc(C(F)(F)F)c4c3C(=O)N(c3ccc(-c5ccccc5CN5CC[C@@H](O)C5)cc3)CN4)cc12

Standard InChI:  InChI=1S/C30H26F3N7O3/c31-30(32,33)27-25-26(40(36-27)20-9-10-24-23(13-20)28(34)37-43-24)29(42)39(16-35-25)19-7-5-17(6-8-19)22-4-2-1-3-18(22)14-38-12-11-21(41)15-38/h1-10,13,21,35,41H,11-12,14-16H2,(H2,34,37)/t21-/m1/s1

Standard InChI Key:  KWXHTGARBNTADQ-OAQYLSRUSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA384129

   1-(3-amino-1,2-benzoxazol-5-yl)-6-[4-(2-{[(3R)-3-hydroxypyrrolidin-1-yl]methyl}phenyl)phenyl]-3-(trifluoromethyl)-1H,4H,5H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

2. Alternative Forms:

   

   ALA384129

   1-(3-amino-1,2-benzoxazol-5-yl)-6-[4-[2-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]phenyl]phenyl]-3-(trifluoromethyl)-4,5-dihydropyrazolo[4,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid

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: 589.58

Molecular Weight (Monoisotopic): 589.2049

AlogP: 4.88

#Rotatable Bonds: 5

Polar Surface Area: 125.68

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.75

CX Basic pKa: 9.13

CX LogP: 4.26

CX LogD: 2.52

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.27

Np Likeness Score: -1.04

References

1. Li YL, Fevig JM, Cacciola J, Buriak J, Rossi KA, Jona J, Knabb RM, Luettgen JM, Wong PC, Bai SA, Wexler RR, Lam PY..  (2006)  Preparation of 1-(3-aminobenzo[d]isoxazol-5-yl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones as potent, selective, and efficacious inhibitors of coagulation factor Xa.,  16  (19): [PMID:16870435] [10.1016/j.bmcl.2006.07.002]

Source

Source(1):

• Scientific Literature