3-{(S)-2-Carboxy-2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-ethyl}-1H-indole-5-carboxylic acid

ID: ALA176905

Chembl Id: CHEMBL176905

PubChem CID: 491140

Max Phase: Preclinical

Molecular Formula: C30H28N4O6

Molecular Weight: 540.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2[nH]cc(C[C@H](NC(=O)c3ccc4c(c3)nc(-c3ccoc3)n4C3CCCCC3)C(=O)O)c2c1

Standard InChI:  InChI=1S/C30H28N4O6/c35-28(33-25(30(38)39)14-20-15-31-23-8-6-18(29(36)37)12-22(20)23)17-7-9-26-24(13-17)32-27(19-10-11-40-16-19)34(26)21-4-2-1-3-5-21/h6-13,15-16,21,25,31H,1-5,14H2,(H,33,35)(H,36,37)(H,38,39)/t25-/m0/s1

Standard InChI Key:  NGIPHNNIDBNJIQ-VWLOTQADSA-N

Alternative Forms

1. Parent:

   

   ALA176905

   3-{(S)-2-Carboxy-2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-ethyl}-1H-indole-5-carboxylic acid

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: 540.58

Molecular Weight (Monoisotopic): 540.2009

AlogP: 5.41

#Rotatable Bonds: 8

Polar Surface Area: 150.45

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.10

CX Basic pKa: 3.59

CX LogP: 4.17

CX LogD: -1.71

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -0.48

References

1. Beaulieu PL, Bös M, Bousquet Y, DeRoy P, Fazal G, Gauthier J, Gillard J, Goulet S, McKercher G, Poupart MA, Valois S, Kukolj G..  (2004)  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency.,  14  (4): [PMID:15013003] [10.1016/j.bmcl.2003.12.032]

Source

Source(1):

• Scientific Literature