6-[4-(4-Acetyl-piperazin-1-yl)-2-fluoro-phenoxymethyl]-7-(2-cyclohexyl-ethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

ID: ALA494517

PubChem CID: 25023785

Max Phase: Preclinical

Molecular Formula: C28H33FN6O2

Molecular Weight: 504.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2ccc(OCc3cc4cnc(C#N)nc4n3CCC3CCCCC3)c(F)c2)CC1

Standard InChI:  InChI=1S/C28H33FN6O2/c1-20(36)33-11-13-34(14-12-33)23-7-8-26(25(29)16-23)37-19-24-15-22-18-31-27(17-30)32-28(22)35(24)10-9-21-5-3-2-4-6-21/h7-8,15-16,18,21H,2-6,9-14,19H2,1H3

Standard InChI Key:  RKKQUNNKTWJTLY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   19.0331   -1.1569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7495   -0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7466    0.0870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0313    0.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3182   -0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3149    0.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5299    0.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0480   -0.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5353   -1.0018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2230   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8076    0.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4646   -1.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -1.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2836   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4773   -1.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2255   -2.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9826    0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5693    1.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7451    1.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3347    0.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7546   -0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5774   -0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072    0.3564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0921    1.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2707    1.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8585    0.3531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2733   -0.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1010   -0.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0335    0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6198    1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6221   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4200   -2.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1675   -3.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7191   -4.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5267   -4.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7827   -3.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9800    1.7979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  6  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 17  1  0
 23 24  1  0
  5  6  2  0
 10 11  1  0
  1  2  2  0
  2 12  1  0
  5  1  1  0
 12 13  3  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 20 23  1  0
  2  3  1  0
 26 29  1  0
  9 14  1  0
 29 30  1  0
 29 31  2  0
 16 32  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
  6  7  1  0
 11 17  1  0
 16 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
  7  8  2  0
 18 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA494517

   7-(2-cyclohexylethyl)-6-[4-(4-acetylpiperazin-1-yl)-2-fluorophenoxymethyl]-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: 504.61

Molecular Weight (Monoisotopic): 504.2649

AlogP: 4.66

#Rotatable Bonds: 7

Polar Surface Area: 87.28

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.34

CX LogP: 4.56

CX LogD: 4.56

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.47

Np Likeness Score: -1.26

References

1. Irie O, Kosaka T, Ehara T, Yokokawa F, Kanazawa T, Hirao H, Iwasaki A, Sakaki J, Teno N, Hitomi Y, Iwasaki G, Fukaya H, Nonomura K, Tanabe K, Koizumi S, Uchiyama N, Bevan SJ, Malcangio M, Gentry C, Fox AJ, Yaqoob M, Culshaw AJ, Allan Hallett..  (2008)  Discovery of orally bioavailable cathepsin S inhibitors for the reversal of neuropathic pain.,  51  (18): [PMID:18754655] [10.1021/jm800839j]

Source

Source(1):

• Scientific Literature