4-[(3-Benzo[1,3]dioxol-5-yl-1-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile

ID: ALA363823

Chembl Id: CHEMBL363823

PubChem CID: 23646754

Max Phase: Preclinical

Molecular Formula: C27H21N5O4

Molecular Weight: 479.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cncc1C(O)(c1ccc(C#N)cc1)c1ccc2c(c1)n(-c1ccc3c(c1)OCO3)c(=O)n2C

Standard InChI:  InChI=1S/C27H21N5O4/c1-30-15-29-14-25(30)27(34,18-5-3-17(13-28)4-6-18)19-7-9-21-22(11-19)32(26(33)31(21)2)20-8-10-23-24(12-20)36-16-35-23/h3-12,14-15,34H,16H2,1-2H3

Standard InChI Key:  JSIKSPRXXVOKDE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA363823

   4-{[3-(2H-1,3-benzodioxol-5-yl)-1-methyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-5-yl](hydroxy)(1-methyl-1H-imidazol-5-yl)methyl}benzonitrile

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: 479.50

Molecular Weight (Monoisotopic): 479.1594

AlogP: 2.95

#Rotatable Bonds: 4

Polar Surface Area: 107.23

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: 5.95

CX LogP: 3.06

CX LogD: 3.05

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.42

Np Likeness Score: -0.95

References

1. Li Q, Li T, Woods KW, Gu WZ, Cohen J, Stoll VS, Galicia T, Hutchins C, Frost D, Rosenberg SH, Sham HL..  (2005)  Benzimidazolones and indoles as non-thiol farnesyltransferase inhibitors based on tipifarnib scaffold: synthesis and activity.,  15  (11): [PMID:15911281] [10.1016/j.bmcl.2005.03.049]

Source

Source(1):

• Scientific Literature