2-(1H-indazol-3-yl)-5-(3-(pyrrolidin-1-yl)propoxy)-1H-benzo[d]imidazole

ID: ALA208775

PubChem CID: 136043808

Max Phase: Preclinical

Molecular Formula: C21H23N5O

Molecular Weight: 361.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc2c(-c3nc4cc(OCCCN5CCCC5)ccc4[nH]3)[nH]nc2c1

Standard InChI:  InChI=1S/C21H23N5O/c1-2-7-17-16(6-1)20(25-24-17)21-22-18-9-8-15(14-19(18)23-21)27-13-5-12-26-10-3-4-11-26/h1-2,6-9,14H,3-5,10-13H2,(H,22,23)(H,24,25)

Standard InChI Key:  GFMYTWVSAZEZRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -7.7792  -18.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9438  -19.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3235  -20.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9982  -18.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3748  -19.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5382  -20.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8177  -20.4441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2091  -19.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5534  -19.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487  -18.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3300  -18.3233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4928  -17.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859  -17.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681  -17.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573  -17.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4630  -16.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1855  -15.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8934  -16.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1945  -15.0439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4848  -14.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4939  -13.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840  -13.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653  -13.7832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0206  -14.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242  -14.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737  -14.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2917  -13.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  2  0
  2  3  2  0
  3  6  1  0
 13 14  2  0
  1  2  1  0
 14 15  1  0
  5  4  1  0
 15 16  2  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 13  1  0
  8  9  1  0
 17 19  1  0
  9  5  2  0
 19 20  1  0
  4  1  2  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
 23 24  1  0
  5  6  1  0
 11 14  1  0
 13 12  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA208775

   ---

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: 361.45

Molecular Weight (Monoisotopic): 361.1903

AlogP: 3.97

#Rotatable Bonds: 6

Polar Surface Area: 69.83

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 9.10

CX LogP: 2.63

CX LogD: 1.32

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.21

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