(R)-N-(1-(3-amino-4-chloro-5-methylbenzo[d]isoxazol-7-yl)pyrrolidin-3-yl)-2-chloro-4-(4H-1,2,4-triazol-4-yl)benzamide

ID: ALA4099310

PubChem CID: 118457032

Max Phase: Preclinical

Molecular Formula: C21H19Cl2N7O2

Molecular Weight: 472.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(N2CC[C@@H](NC(=O)c3ccc(-n4cnnc4)cc3Cl)C2)c2onc(N)c2c1Cl

Standard InChI:  InChI=1S/C21H19Cl2N7O2/c1-11-6-16(19-17(18(11)23)20(24)28-32-19)29-5-4-12(8-29)27-21(31)14-3-2-13(7-15(14)22)30-9-25-26-10-30/h2-3,6-7,9-10,12H,4-5,8H2,1H3,(H2,24,28)(H,27,31)/t12-/m1/s1

Standard InChI Key:  WRLGJSVRFOTDKJ-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   21.0186  -10.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0174  -11.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7255  -11.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4351  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4323  -10.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7237  -10.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3108  -10.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3106   -9.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6031  -10.7394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8953  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8093   -9.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0099   -9.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6015  -10.0574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1485  -10.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7908  -10.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3107   -9.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4987   -9.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1658  -10.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4613  -10.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6475  -10.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4840  -11.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1968  -12.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8006  -11.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7403  -12.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7212   -9.5130    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.1435  -11.9656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2307  -12.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0303  -12.9444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4378  -12.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8900  -11.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3530  -10.3989    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0185   -8.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  7  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 20  1  0
 19 15  1  0
 13 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 21 24  1  0
  6 25  1  0
  4 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 18 31  1  0
 17 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099310

   US9969724, Example 12

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: 472.34

Molecular Weight (Monoisotopic): 471.0977

AlogP: 3.61

#Rotatable Bonds: 4

Polar Surface Area: 115.10

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.61

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -1.75

References

1. Sakurada I, Endo T, Hikita K, Hirabayashi T, Hosaka Y, Kato Y, Maeda Y, Matsumoto S, Mizuno T, Nagasue H, Nishimura T, Shimada S, Shinozaki M, Taguchi K, Takeuchi K, Yokoyama T, Hruza A, Reichert P, Zhang T, Wood HB, Nakao K, Furusako S..  (2017)  Discovery of novel aminobenzisoxazole derivatives as orally available factor IXa inhibitors.,  27  (11): [PMID:28408226] [10.1016/j.bmcl.2017.03.002]

Source

Source(1):

• Scientific Literature