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

ID: ALA249966

PubChem CID: 10046162

Max Phase: Preclinical

Molecular Formula: C21H26N6O2

Molecular Weight: 394.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)Cn1c(CN2C(=O)CC3(CCNCC3)C2=O)cc2cnc(C#N)nc21

Standard InChI:  InChI=1S/C21H26N6O2/c1-20(2,3)13-27-15(8-14-11-24-16(10-22)25-18(14)27)12-26-17(28)9-21(19(26)29)4-6-23-7-5-21/h8,11,23H,4-7,9,12-13H2,1-3H3

Standard InChI Key:  GXGLUMCONRSMLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.1551   -5.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6718   -5.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2196   -4.4881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4238   -4.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9504   -5.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9504   -6.3571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6650   -6.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3839   -6.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6206   -3.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4455   -3.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9429   -4.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9213   -3.0735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7100   -3.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7194   -4.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4348   -4.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1415   -4.1191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1281   -3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4120   -2.8964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4973   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8972   -1.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724   -0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7221   -1.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3305   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8357   -2.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5443   -2.4452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4958   -5.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7806   -4.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0
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  8  9  1  0
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  9  1  1  0
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  1 10  1  0
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  5  1  1  0
 22 23  1  0
  4 11  1  0
 22 24  1  0
  6  7  1  0
 22 25  1  0
 11 12  1  0
 19 26  1  0
 12 13  2  0
 26 27  3  0
  1  2  1  0
  3 28  2  0
  5 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA249966

   7-(2,2-dimethyl-propyl)-6-(1,3-dioxo-2,8-diaza-spiro[4.5]dec-2-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: 394.48

Molecular Weight (Monoisotopic): 394.2117

AlogP: 1.98

#Rotatable Bonds: 3

Polar Surface Area: 103.91

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.14

CX LogP: 1.80

CX LogD: -0.85

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.80

Np Likeness Score: -0.74

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]

3. Allen JG, Fotsch C, Babij P..  (2010)  Emerging targets in osteoporosis disease modification.,  53  (11): [PMID:20218623] [10.1021/jm9018756]

4. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data