2-Cyano-4-[(spiro[2.5]oct-6-ylmethyl)-amino]-pyrimidine-5-carboxylic acid (1-methyl-4-phenyl-piperidin-4-ylmethyl)-amide

ID: ALA508319

PubChem CID: 44587937

Max Phase: Preclinical

Molecular Formula: C28H36N6O

Molecular Weight: 472.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC(CNC(=O)c2cnc(C#N)nc2NCC2CCC3(CC2)CC3)(c2ccccc2)CC1

Standard InChI:  InChI=1S/C28H36N6O/c1-34-15-13-28(14-16-34,22-5-3-2-4-6-22)20-32-26(35)23-19-30-24(17-29)33-25(23)31-18-21-7-9-27(10-8-21)11-12-27/h2-6,19,21H,7-16,18,20H2,1H3,(H,32,35)(H,30,31,33)

Standard InChI Key:  FJKPOCSUBVDARQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.1833    0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    0.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1753   -4.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7587   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5840   -3.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288   -2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390   -2.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0435   -3.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3244   -3.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6127   -1.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019   -0.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6157    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3308   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7568   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7528   -0.2153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0380    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4724   -1.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1892   -1.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7400    1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    0.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -0.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -0.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4718   -1.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562   -1.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7568   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886   -2.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845   -1.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104    0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1  3  1  0
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  9 10  1  0
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 18 13  1  0
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 20 23  1  0
  5 11  1  0
 23 24  3  0
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  5  4  1  0
  7 13  1  0
  6  5  1  0
  1 28  1  0
  3 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  2 14  1  0
  1 29  1  0
  7  8  1  0
 29 30  2  0
 14 15  1  0
 30 31  1  0
  8  9  1  0
 31 32  2  0
 15 16  1  0
 32 33  1  0
  4  6  1  0
 33 34  2  0
 34 29  1  0
 15 17  2  0
 26 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA508319

   2-cyano-N-[(1-methyl-4-phenylpiperidin-4-yl)methyl]-4-(spiro[2.5]octan-6-ylmethylamino)pyrimidine-5-carboxamide

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: 472.64

Molecular Weight (Monoisotopic): 472.2951

AlogP: 4.12

#Rotatable Bonds: 7

Polar Surface Area: 93.94

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 8.88

CX LogP: 4.71

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.63

Np Likeness Score: -0.67

References

1. Irie O, Yokokawa F, Ehara T, Iwasaki A, Iwaki Y, Hitomi Y, Konishi K, Kishida M, Toyao A, Masuya K, Gunji H, Sakaki J, Iwasaki G, Hirao H, Kanazawa T, Tanabe K, Kosaka T, Hart TW, Hallett A..  (2008)  4-Amino-2-cyanopyrimidines: novel scaffold for nonpeptidic cathepsin S inhibitors.,  18  (16): [PMID:18662880] [10.1016/j.bmcl.2008.07.011]

Source

Source(1):

• Scientific Literature