2-chloro-N-(3-methyl-1-(4-methyl-2-nitrophenyl)pyrrolidin-3-yl)-4-(4H-1,2,4-triazol-4-yl)benzamide

ID: ALA4071351

PubChem CID: 137638513

Max Phase: Preclinical

Molecular Formula: C21H21ClN6O3

Molecular Weight: 440.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2CCC(C)(NC(=O)c3ccc(-n4cnnc4)cc3Cl)C2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C21H21ClN6O3/c1-14-3-6-18(19(9-14)28(30)31)26-8-7-21(2,11-26)25-20(29)16-5-4-15(10-17(16)22)27-12-23-24-13-27/h3-6,9-10,12-13H,7-8,11H2,1-2H3,(H,25,29)

Standard InChI Key:  CNNWJYRXNDWIEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    9.6500   -6.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9372   -6.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9362   -7.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1160   -6.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1982   -5.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5287   -5.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -5.7809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0782   -5.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -4.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254   -4.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5113   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6868   -5.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4708   -6.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6467   -6.8865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362   -7.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329   -7.1374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259   -4.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3652   -6.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0795   -6.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3663   -5.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0760   -7.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7894   -8.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5057   -7.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5041   -6.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7900   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7877   -5.7413    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.2206   -8.2186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3095   -9.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1169   -9.2080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5294   -8.4931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9770   -7.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11 17  1  0
  1 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
 25 26  1  0
 23 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 27  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4071351

   ---

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: 440.89

Molecular Weight (Monoisotopic): 440.1364

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 106.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.65

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -1.81

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