7-(2,2-dimethylpropyl)-6-{5-fluoro-2-oxo-1,2-dihydrospiro[indole-3,4'-piperidine]-1-ylmethyl}-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

ID: ALA400395

PubChem CID: 10478741

Max Phase: Preclinical

Molecular Formula: C25H27FN6O

Molecular Weight: 446.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)Cn1c(CN2C(=O)C3(CCNCC3)c3cc(F)ccc32)cc2cnc(C#N)nc21

Standard InChI:  InChI=1S/C25H27FN6O/c1-24(2,3)15-32-18(10-16-13-29-21(12-27)30-22(16)32)14-31-20-5-4-17(26)11-19(20)25(23(31)33)6-8-28-9-7-25/h4-5,10-11,13,28H,6-9,14-15H2,1-3H3

Standard InChI Key:  RDHIHRXXXLHRIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -6.1003  -11.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1045  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120  -12.6624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5114  -10.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5114  -11.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8055  -11.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0953  -10.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8055  -10.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7652  -12.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0579  -13.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2509  -13.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9175  -14.3802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345  -13.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208  -13.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975  -14.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4908  -14.8446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071  -14.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336  -13.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1417  -13.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952  -15.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854  -15.7018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3281  -15.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170  -15.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067  -16.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006  -15.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6311  -16.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3052  -11.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8243  -12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045  -11.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645  -11.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1464  -10.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645  -10.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8092   -9.7441    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  5  6  1  0
 15 16  1  0
  6  1  1  0
 16 17  2  0
  1  7  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 17 20  1  0
  2  9  2  0
 20 21  3  0
  1  2  1  0
 12 22  1  0
  3 10  1  0
 22 23  1  0
 23 24  1  0
 10 11  1  0
 23 25  1  0
 11 12  1  0
 23 26  1  0
  2  3  1  0
  3 28  1  0
 27 28  2  0
 12 15  1  0
 28 29  1  0
 14 13  1  0
 29 30  2  0
 13 11  2  0
 30 31  1  0
 27  1  1  0
 31 32  2  0
 32 27  1  0
  4  8  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA400395

   7-(2,2-Dimethylpropyl)-6-[(5-fluoro-2-oxospiro[indole-3,4'-piperidine]-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile

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: 446.53

Molecular Weight (Monoisotopic): 446.2230

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 86.84

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.77

CX LogP: 3.68

CX LogD: 1.35

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.66

Np Likeness Score: -0.81

References

1. Teno N, Miyake T, Ehara T, Irie O, Sakaki J, Ohmori O, Gunji H, Matsuura N, Masuya K, Hitomi Y, Nonomura K, Horiuchi M, Gohda K, Iwasaki A, Umemura I, Tada S, Kometani M, Iwasaki G, Cowan-Jacob SW, Missbach M, Lattmann R, Betschart C..  (2007)  Novel scaffold for cathepsin K inhibitors.,  17  (22): [PMID:17911019] [10.1016/j.bmcl.2007.09.047]

2. Teno N, Masuya K, Ehara T, Kosaka T, Miyake T, Irie O, Hitomi Y, Matsuura N, Umemura I, Iwasaki G, Fukaya H, Toriyama K, Uchiyama N, Nonomura K, Sugiyama I, Kometani M..  (2008)  Effect of cathepsin K inhibitors on bone resorption.,  51  (17): [PMID:18707091] [10.1021/jm800626a]

Source

Source(1):

• Scientific Literature