7-(2,2-dimethyl-propyl)-6-(3-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

ID: ALA249965

PubChem CID: 10272927

Max Phase: Preclinical

Molecular Formula: C21H27N7O2

Molecular Weight: 409.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)NC2(CCN(Cc3cc4cnc(C#N)nc4n3CC(C)(C)C)CC2)C1=O

Standard InChI:  InChI=1S/C21H27N7O2/c1-20(2,3)13-28-15(9-14-11-23-16(10-22)24-17(14)28)12-27-7-5-21(6-8-27)18(29)26(4)19(30)25-21/h9,11H,5-8,12-13H2,1-4H3,(H,25,30)

Standard InChI Key:  USHMVOYUHZUPCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
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   -6.6499    2.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4723    2.3218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7717    1.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1245    1.0254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4271    0.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144    0.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    0.6551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    1.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144    1.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5673    1.3321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9314    3.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1365    2.9244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871    0.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    0.3174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    1.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642   -0.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1007   -1.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    0.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790    1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726    0.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532    0.9322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393    1.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    2.3568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729    2.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141    1.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095    1.6462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 14 15  1  0
 15 16  1  0
  3  4  1  0
  4  5  1  0
 16 24  1  0
 23 17  1  0
 17 15  2  0
  1 10  1  0
 16 18  1  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 19 21  1  0
  9 10  1  0
 19 22  1  0
  5  1  1  0
  4 11  2  0
 23 24  2  0
  1  6  1  0
 24 25  1  0
  3 12  1  0
 25 26  2  0
  1  2  1  0
 26 27  1  0
  2 13  2  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
  8 14  1  0
 29 30  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA249965

   7-(2,2-dimethyl-propyl)-6-(3-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl)-7H-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: 409.49

Molecular Weight (Monoisotopic): 409.2226

AlogP: 1.87

#Rotatable Bonds: 3

Polar Surface Area: 107.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: 7.63

CX LogP: 1.60

CX LogD: 1.17

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.78

Np Likeness Score: -1.10

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