4-(2-(4-chloro-1H-pyrazol-1-yl)ethylamino)-3-(6-(1-(3-fluoropropyl)piperidin-4-yl)-4-methyl-1H-bendo[d]imidazol-2-yl)pyridine-1-(1H)-one

ID: ALA459729

PubChem CID: 135441202

Max Phase: Preclinical

Molecular Formula: C26H31ClFN7O

Molecular Weight: 512.03

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BMS-695735

Canonical SMILES:  Cc1cc(C2CCN(CCCF)CC2)cc2[nH]c(-c3c(NCCn4cc(Cl)cn4)cc[nH]c3=O)nc12

Standard InChI:  InChI=1S/C26H31ClFN7O/c1-17-13-19(18-4-10-34(11-5-18)9-2-6-28)14-22-24(17)33-25(32-22)23-21(3-7-30-26(23)36)29-8-12-35-16-20(27)15-31-35/h3,7,13-16,18H,2,4-6,8-12H2,1H3,(H,32,33)(H2,29,30,36)

Standard InChI Key:  VWELCPLMPPEKOL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.5194   -9.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5182  -10.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2331  -11.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2313   -9.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9466   -9.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9469  -10.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7374  -11.0798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2257  -10.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7369   -9.7352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8028   -8.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0923   -8.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3755   -8.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3737   -9.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0888   -9.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0508  -10.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4623  -11.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2837  -11.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6998  -10.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2883   -9.6975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4606   -9.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0417   -8.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0483  -11.8384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4593  -12.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0454  -13.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4564  -13.9827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2333  -12.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6625   -8.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9466   -8.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2336   -8.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5177   -8.7399    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1238  -14.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7358  -15.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4512  -14.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2812  -14.0699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6479  -16.1085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  1  0
 16 21  1  0
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  8 16  1  0
  4  1  1  0
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  5  6  1  0
 17 23  1  0
 23 24  1  0
  2  3  1  0
 24 25  1  0
  3  6  2  0
 25 26  1  0
  1  2  2  0
  3 27  1  0
 10 15  1  0
 13 28  1  0
 11 12  1  0
 28 29  1  0
 12 13  1  0
 29 30  1  0
 13 14  1  0
 30 31  1  0
 26 32  1  0
 14 15  1  0
  1 10  1  0
 16 17  2  0
  5  4  2  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 26  1  0
  6  7  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA459729

   ---

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: 512.03

Molecular Weight (Monoisotopic): 511.2263

AlogP: 4.73

#Rotatable Bonds: 9

Polar Surface Area: 94.63

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.30

CX Basic pKa: 9.13

CX LogP: 2.29

CX LogD: 0.93

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: -1.38

References

1. Velaparthi U, Wittman M, Liu P, Carboni JM, Lee FY, Attar R, Balimane P, Clarke W, Sinz MW, Hurlburt W, Patel K, Discenza L, Kim S, Gottardis M, Greer A, Li A, Saulnier M, Yang Z, Zimmermann K, Trainor G, Vyas D..  (2008)  Discovery and evaluation of 4-(2-(4-chloro-1H-pyrazol-1-yl)ethylamino)-3-(6-(1-(3-fluoropropyl)piperidin-4-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one (BMS-695735), an orally efficacious inhibitor of insulin-like growth factor-1 receptor kinase with broad spectrum in vivo antitumor activity.,  51  (19): [PMID:18763755] [10.1021/jm800832q]

Source

Source(1):

• Scientific Literature