N-benzyl-1-isopropyl-6-methoxy-1H-benzo[d]imidazol-4-amine

ID: ALA1096834

PubChem CID: 44143116

Max Phase: Preclinical

Molecular Formula: C18H21N3O

Molecular Weight: 295.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NCc2ccccc2)c2ncn(C(C)C)c2c1

Standard InChI:  InChI=1S/C18H21N3O/c1-13(2)21-12-20-18-16(9-15(22-3)10-17(18)21)19-11-14-7-5-4-6-8-14/h4-10,12-13,19H,11H2,1-3H3

Standard InChI Key:  XNTDNBYHJFCUMA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -4.9199    1.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    0.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2082    0.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    1.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102    2.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793    2.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    1.7988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588    0.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7712    0.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -0.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    0.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388   -0.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577   -0.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.8266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512   -1.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663   -1.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4801   -0.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1965   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
 12 14  1  0
 13  9  1  0
 13 14  2  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 15 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
  9 10  2  0
 11 21  1  0
  2  3  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096834

   Benzyl-(1-isopropyl-6-methoxy-benzimidazol-4-yl)amine

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: 295.39

Molecular Weight (Monoisotopic): 295.1685

AlogP: 4.24

#Rotatable Bonds: 5

Polar Surface Area: 39.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.21

CX LogP: 3.30

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -0.96

References

1. Flaherty PT, Chopra I, Jain P, Yi S, Allen E, Cavanaugh J..  (2010)  Identification of benzimidazole-based inhibitors of the mitogen activated kinase-5 signaling pathway.,  20  (9): [PMID:20382528] [10.1016/j.bmcl.2010.03.033]

2. Flaherty PT, Chopra I, Jain P, Monlish D, Cavanaugh J..  (2010)  Structure-activity relationships of benzimidazole-based selective inhibitors of the mitogen activated kinase-5 signaling pathway.,  18  (22): [PMID:20965737] [10.1016/j.bmc.2010.09.017]

3. PubChem BioAssay data set, 

4. Jain P, Flaherty PT, Yi S, Chopra I, Bleasdell G, Lipay J, Ferandin Y, Meijer L, Madura JD..  (2011)  Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25.,  19  (1): [PMID:21144757] [10.1016/j.bmc.2010.11.022]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays