(R)-N-(1-(3-amino-4-chloroisoxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(3-(difluoromethyl)-4H-1,2,4-triazol-4-yl)benzamide

ID: ALA4085239

PubChem CID: 118456915

Max Phase: Preclinical

Molecular Formula: C20H16Cl2F2N8O2

Molecular Weight: 509.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1noc2c(N3CC[C@@H](NC(=O)c4ccc(-n5cnnc5C(F)F)cc4Cl)C3)ncc(Cl)c12

Standard InChI:  InChI=1S/C20H16Cl2F2N8O2/c21-12-5-10(32-8-27-29-19(32)16(23)24)1-2-11(12)20(33)28-9-3-4-31(7-9)18-15-14(13(22)6-26-18)17(25)30-34-15/h1-2,5-6,8-9,16H,3-4,7H2,(H2,25,30)(H,28,33)/t9-/m1/s1

Standard InChI Key:  NIYMWAUKEZOKLD-SECBINFHSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    8.8928   -4.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916   -4.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5997   -5.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3093   -4.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3065   -4.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5979   -3.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1850   -3.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7695   -3.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6835   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8841   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757   -3.3342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0227   -3.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6650   -3.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -2.7589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729   -2.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3355   -4.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -4.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -5.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710   -5.4643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -4.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145   -5.3994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5954   -2.7897    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -3.6756    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0137   -5.2404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1004   -6.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9000   -6.2216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3075   -5.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7597   -4.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9283   -4.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7051   -3.8535    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3201   -3.5614    0.0000 F   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
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  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
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 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
 18 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 27  1  0
  4 27  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085239

   N-[(3R)-1-(3-amino-4-chloro-[1,2]oxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl]-2-chloro-4-[3-(difluoromethyl)-1,2,4-triazol-4-yl]benzamide

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: 509.30

Molecular Weight (Monoisotopic): 508.0741

AlogP: 3.64

#Rotatable Bonds: 5

Polar Surface Area: 127.99

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.99

CX Basic pKa: 1.16

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -2.10

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