2-[(6'-fluoro-2'-oxo-spiro[cyclopropane-1,3'-indoline]-1'-yl)methyl]-1-(4,4,4-trifluorobutyl)benzimidazole-5-carboxamidine

ID: ALA4855358

PubChem CID: 164617986

Max Phase: Preclinical

Molecular Formula: C23H21F4N5O

Molecular Weight: 459.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2c(c1)nc(CN1C(=O)C3(CC3)c3ccc(F)cc31)n2CCCC(F)(F)F

Standard InChI:  InChI=1S/C23H21F4N5O/c24-14-3-4-15-18(11-14)32(21(33)22(15)7-8-22)12-19-30-16-10-13(20(28)29)2-5-17(16)31(19)9-1-6-23(25,26)27/h2-5,10-11H,1,6-9,12H2,(H3,28,29)

Standard InChI Key:  IUNZGXGVPQEGFJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    9.8914   -4.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3082   -5.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7205   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8245   -8.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5409   -7.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5380   -6.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8227   -6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1096   -7.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1063   -6.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3214   -6.5305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8394   -7.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3267   -7.8642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0144   -7.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991   -6.4899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9274   -5.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7742   -6.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6015   -5.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8189   -5.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2083   -5.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3856   -6.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1680   -6.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7331   -5.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7764   -7.2692    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0750   -8.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6295   -9.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3777  -10.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9323  -10.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6805  -11.4428    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7385  -10.4823    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5122  -11.2372    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.2510   -6.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9669   -6.7699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2478   -5.5352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  1  3  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  2 17  1  0
 16 14  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 15 22  2  0
 20 23  1  0
 12 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  6 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4855358

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.45

Molecular Weight (Monoisotopic): 459.1682

AlogP: 4.38

#Rotatable Bonds: 6

Polar Surface Area: 88.00

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.80

CX LogP: 3.46

CX LogD: 1.08

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -1.21

References

1. Cockerill GS, Angell RM, Bedernjak A, Chuckowree I, Fraser I, Gascon-Simorte J, Gilman MSA, Good JAD, Harland R, Johnson SM, Ludes-Meyers JH, Littler E, Lumley J, Lunn G, Mathews N, McLellan JS, Paradowski M, Peeples ME, Scott C, Tait D, Taylor G, Thom M, Thomas E, Villalonga Barber C, Ward SE, Watterson D, Williams G, Young P, Powell K..  (2021)  Discovery of Sisunatovir (RV521), an Inhibitor of Respiratory Syncytial Virus Fusion.,  64  (7.0): [PMID:33729773] [10.1021/acs.jmedchem.0c01882]

Source

Source(1):

• Scientific Literature