methyl 3-(5-(4-(piperidin-1-yl)piperidin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-indazole-5-carboxylate

ID: ALA380372

PubChem CID: 136043801

Max Phase: Preclinical

Molecular Formula: C26H30N6O2

Molecular Weight: 458.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc2[nH]nc(-c3nc4cc(N5CCC(N6CCCCC6)CC5)ccc4[nH]3)c2c1

Standard InChI:  InChI=1S/C26H30N6O2/c1-34-26(33)17-5-7-21-20(15-17)24(30-29-21)25-27-22-8-6-19(16-23(22)28-25)32-13-9-18(10-14-32)31-11-3-2-4-12-31/h5-8,15-16,18H,2-4,9-14H2,1H3,(H,27,28)(H,29,30)

Standard InChI Key:  HUQYQFBIFGUUQQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -4.7548   -5.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7618   -6.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0520   -6.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426   -4.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3327   -6.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481   -6.2662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581   -5.6005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   -4.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2801   -4.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.9008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7604   -3.4806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2717   -2.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3113    0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657   -0.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.7671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8545    2.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963    3.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164    2.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559    2.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4664   -4.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -3.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1852   -5.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480   -3.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
 18 13  2  0
  8  9  2  0
 17 19  1  0
 19 20  1  0
  9  5  1  0
  4  1  2  0
  9 10  1  0
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  5  6  2  0
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 20 21  1  0
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 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 11 14  1  0
 13 12  1  0
 12 10  2  0
  2  3  2  0
  3  6  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 14  1  0
  1 31  1  0
  1  2  1  0
 14 15  2  0
 31 32  1  0
 31 33  2  0
  5  4  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA380372

   ---

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: 458.57

Molecular Weight (Monoisotopic): 458.2430

AlogP: 4.35

#Rotatable Bonds: 4

Polar Surface Area: 90.14

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.68

CX Basic pKa: 9.76

CX LogP: 3.68

CX LogD: 1.60

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -1.18

References

1. McBride CM, Renhowe PA, Heise C, Jansen JM, Lapointe G, Ma S, Piñeda R, Vora J, Wiesmann M, Shafer CM..  (2006)  Design and structure-activity relationship of 3-benzimidazol-2-yl-1H-indazoles as inhibitors of receptor tyrosine kinases.,  16  (13): [PMID:16603352] [10.1016/j.bmcl.2006.03.069]

Source

Source(1):

• Scientific Literature