3-Cyclohexyl-1-methyl-2-phenyl-1H-indole-6-carboxylic acid

ID: ALA425693

Chembl Id: CHEMBL425693

PubChem CID: 514257

Max Phase: Preclinical

Molecular Formula: C22H23NO2

Molecular Weight: 333.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccccc2)c(C2CCCCC2)c2ccc(C(=O)O)cc21

Standard InChI:  InChI=1S/C22H23NO2/c1-23-19-14-17(22(24)25)12-13-18(19)20(15-8-4-2-5-9-15)21(23)16-10-6-3-7-11-16/h3,6-7,10-15H,2,4-5,8-9H2,1H3,(H,24,25)

Standard InChI Key:  BTHWMJUPMGCKFS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA425693

   3-Cyclohexyl-1-methyl-2-phenyl-indole-6-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: 333.43

Molecular Weight (Monoisotopic): 333.1729

AlogP: 5.59

#Rotatable Bonds: 3

Polar Surface Area: 42.23

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.62

CX Basic pKa:

CX LogP: 5.64

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -0.14

References

1. Harper S, Pacini B, Avolio S, Di Filippo M, Migliaccio G, Laufer R, De Francesco R, Rowley M, Narjes F..  (2005)  Development and preliminary optimization of indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase.,  48  (5): [PMID:15743173] [10.1021/jm049122i]

2. Beaulieu PL, Gillard J, Bykowski D, Brochu C, Dansereau N, Duceppe JS, Haché B, Jakalian A, Lagacé L, LaPlante S, McKercher G, Moreau E, Perreault S, Stammers T, Thauvette L, Warrington J, Kukolj G..  (2006)  Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCV NS5B polymerase: from benzimidazole to indole scaffolds.,  16  (19): [PMID:16908138] [10.1016/j.bmcl.2006.07.074]

3. Meanwell NA..  (2016)  2015 Philip S. Portoghese Medicinal Chemistry Lectureship. Curing Hepatitis C Virus Infection with Direct-Acting Antiviral Agents: The Arc of a Medicinal Chemistry Triumph.,  59  (16): [PMID:27501244] [10.1021/acs.jmedchem.6b00915]

Source

Source(1):

• Scientific Literature