2-(4-(benzylamino)-1-cyclopentyl-1H-benzo[d]imidazol-6-yloxy)butan-1-ol

ID: ALA1098843

PubChem CID: 44141948

Max Phase: Preclinical

Molecular Formula: C23H29N3O2

Molecular Weight: 379.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CO)Oc1cc(NCc2ccccc2)c2ncn(C3CCCC3)c2c1

Standard InChI:  InChI=1S/C23H29N3O2/c1-2-19(15-27)28-20-12-21(24-14-17-8-4-3-5-9-17)23-22(13-20)26(16-25-23)18-10-6-7-11-18/h3-5,8-9,12-13,16,18-19,24,27H,2,6-7,10-11,14-15H2,1H3

Standard InChI Key:  WGXYUMXKMNTQPP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.2372  -10.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360  -11.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496  -11.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6696  -11.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664  -10.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9476  -10.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3796  -10.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0967  -10.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007  -11.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3877  -11.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915  -12.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1092  -13.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8174  -11.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8213  -12.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6031  -12.9467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0823  -12.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5967  -11.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0099  -13.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6782  -13.1265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819  -13.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7425  -14.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3930  -14.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0669  -14.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8326  -13.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686  -14.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2516  -13.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988  -14.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4026  -15.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 11 19  1  0
  4  5  1  0
 19 20  1  0
 18 21  1  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 11 12  2  0
 20 25  1  0
 12 14  1  0
 25 26  1  0
 13  9  1  0
 20 27  1  0
 13 14  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098843

   2-[7-(Benzylamino)-3-cyclopentylbenzimidazol-5-yl]oxybutan-1-ol

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: 379.50

Molecular Weight (Monoisotopic): 379.2260

AlogP: 4.91

#Rotatable Bonds: 8

Polar Surface Area: 59.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.18

CX LogP: 4.13

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.36

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. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays