1'-[[5-(aminomethyl)-1-(4-hydroxybutyl)benzimidazol-2-yl]methyl]-6'-fluoro-spiro[cyclopropane-1,3'-indoline]-2'-one

ID: ALA4853602

PubChem CID: 164612285

Max Phase: Preclinical

Molecular Formula: C23H25FN4O2

Molecular Weight: 408.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1ccc2c(c1)nc(CN1C(=O)C3(CC3)c3ccc(F)cc31)n2CCCCO

Standard InChI:  InChI=1S/C23H25FN4O2/c24-16-4-5-17-20(12-16)28(22(30)23(17)7-8-23)14-21-26-18-11-15(13-25)3-6-19(18)27(21)9-1-2-10-29/h3-6,11-12,29H,1-2,7-10,13-14,25H2

Standard InChI Key:  VZKVSUCQBRRADM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    7.1586   -5.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5709   -4.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6751   -7.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3915   -7.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3886   -6.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6732   -6.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9602   -7.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9568   -6.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1719   -6.4058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6899   -7.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1772   -7.7396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1016   -6.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8176   -6.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650   -7.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9254   -8.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4495   -6.3652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7778   -5.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -6.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4519   -5.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6692   -5.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -6.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0183   -6.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5839   -5.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266   -7.1444    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4800   -9.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2282   -9.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7828  -10.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5310  -11.3183    0.0000 O   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
  6 13  1  0
 13 14  1  0
 11 15  1  0
 12 16  1  0
 15 17  1  0
 17 18  1  0
 18  2  1  0
  2 20  1  0
 19 17  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 25  2  0
 23 26  1  0
 16 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4853602

   ---

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: 408.48

Molecular Weight (Monoisotopic): 408.1962

AlogP: 2.99

#Rotatable Bonds: 7

Polar Surface Area: 84.38

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.08

CX LogP: 2.03

CX LogD: 0.37

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -0.97

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