2-(1H-indazol-3-yl)-5-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole

ID: ALA209265

PubChem CID: 136038492

Max Phase: Preclinical

Molecular Formula: C20H22N6

Molecular Weight: 346.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(Cc2ccc3[nH]c(-c4[nH]nc5ccccc45)nc3c2)CC1

Standard InChI:  InChI=1S/C20H22N6/c1-25-8-10-26(11-9-25)13-14-6-7-17-18(12-14)22-20(21-17)19-15-4-2-3-5-16(15)23-24-19/h2-7,12H,8-11,13H2,1H3,(H,21,22)(H,23,24)

Standard InChI Key:  DLHYZQMLROULHQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   -0.4378  -18.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029  -19.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137  -20.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393  -18.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9619  -19.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986  -20.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187  -20.4532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271  -19.8937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829  -19.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876  -18.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059  -18.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435  -17.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502  -17.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677  -17.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781  -17.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724  -16.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502  -15.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427  -16.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1412  -15.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506  -14.6355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640  -15.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714  -14.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2665  -13.8008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481  -13.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345  -13.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9776  -13.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  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
 20 21  1  0
  4  1  2  0
  9 10  1  0
 10 11  1  0
  5  6  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 11 14  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209265

   ---

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: 346.44

Molecular Weight (Monoisotopic): 346.1906

AlogP: 2.85

#Rotatable Bonds: 3

Polar Surface Area: 63.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.54

CX Basic pKa: 7.90

CX LogP: 2.53

CX LogD: 2.04

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: -1.28

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