(S)-2-[(1-Cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-3-(5-hydroxy-1H-indol-3-yl)-propionic acid

ID: ALA367225

Chembl Id: CHEMBL367225

PubChem CID: 491128

Max Phase: Preclinical

Molecular Formula: C29H28N4O5

Molecular Weight: 512.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccoc1)n2C1CCCCC1

Standard InChI:  InChI=1S/C29H28N4O5/c34-21-7-8-23-22(14-21)19(15-30-23)13-25(29(36)37)32-28(35)17-6-9-26-24(12-17)31-27(18-10-11-38-16-18)33(26)20-4-2-1-3-5-20/h6-12,14-16,20,25,30,34H,1-5,13H2,(H,32,35)(H,36,37)/t25-/m0/s1

Standard InChI Key:  BSDJZQSNAUWLEB-VWLOTQADSA-N

Alternative Forms

1. Parent:

   

   ALA367225

   (2S)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]-3-(5-hydroxy-1H-indol-3-yl)propanoic 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: 512.57

Molecular Weight (Monoisotopic): 512.2060

AlogP: 5.41

#Rotatable Bonds: 7

Polar Surface Area: 133.38

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.96

CX Basic pKa: 3.31

CX LogP: 4.40

CX LogD: 1.71

Aromatic Rings: 5

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: -0.36

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]

2. Beaulieu PL, Bousquet Y, Gauthier J, Gillard J, Marquis M, McKercher G, Pellerin C, Valois S, Kukolj G..  (2004)  Non-nucleoside benzimidazole-based allosteric inhibitors of the hepatitis C virus NS5B polymerase: inhibition of subgenomic hepatitis C virus RNA replicons in Huh-7 cells.,  47  (27): [PMID:15615537] [10.1021/jm040134d]

3. Beaulieu PL, Dansereau N, Duan J, Garneau M, Gillard J, McKercher G, LaPlante S, Lagacée L, Thauvette L, Kukolj G..  (2010)  Benzimidazole Thumb Pocket I finger-loop inhibitors of HCV NS5B polymerase: improved drug-like properties through C-2 SAR in three sub-series.,  20  (6): [PMID:20185309] [10.1016/j.bmcl.2010.02.003]

Source

Source(1):

• Scientific Literature