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

ID: ALA4092982

PubChem CID: 118457019

Max Phase: Preclinical

Molecular Formula: C22H21Cl2N7O3

Molecular Weight: 502.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1noc2c(N3CC[C@@H](NC(=O)c4ccc(-n5cnc(CCO)c5)cc4Cl)C3)ncc(Cl)c12

Standard InChI:  InChI=1S/C22H21Cl2N7O3/c23-16-7-14(31-9-12(4-6-32)27-11-31)1-2-15(16)22(33)28-13-3-5-30(10-13)21-19-18(17(24)8-26-21)20(25)29-34-19/h1-2,7-9,11,13,32H,3-6,10H2,(H2,25,29)(H,28,33)/t13-/m1/s1

Standard InChI Key:  BGGBGEFMFFHNBU-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

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    8.9888  -20.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6985  -19.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0542  -18.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4601  -20.5905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640  -20.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037  -20.5257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846  -17.9160    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6164  -18.8019    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4073  -20.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4941  -21.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2937  -21.3474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7012  -20.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1534  -20.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5138  -20.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9952  -21.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8078  -21.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
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  7  8  2  0
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 10  9  1  1
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 20 21  1  0
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 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
 30 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092982

   N-[(3R)-1-(3-amino-4-chloro-[1,2]oxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl]-2-chloro-4-[4-(2-hydroxyethyl)imidazol-1-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: 502.36

Molecular Weight (Monoisotopic): 501.1083

AlogP: 2.84

#Rotatable Bonds: 6

Polar Surface Area: 135.33

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.75

CX LogP: 1.95

CX LogD: 1.94

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: -1.52

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