5-{4-[1-(5-chlorothiophen-2-ylmethyl)-6-fluoro-1H-indol-3-yl]piperidin-1-ylmethyl}-2-methoxybenzoic acid

ID: ALA221730

Chembl Id: CHEMBL221730

PubChem CID: 10279311

Max Phase: Preclinical

Molecular Formula: C27H26ClFN2O3S

Molecular Weight: 513.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CN2CCC(c3cn(Cc4ccc(Cl)s4)c4cc(F)ccc34)CC2)cc1C(=O)O

Standard InChI:  InChI=1S/C27H26ClFN2O3S/c1-34-25-6-2-17(12-22(25)27(32)33)14-30-10-8-18(9-11-30)23-16-31(15-20-4-7-26(28)35-20)24-13-19(29)3-5-21(23)24/h2-7,12-13,16,18H,8-11,14-15H2,1H3,(H,32,33)

Standard InChI Key:  KQSXGBBQVLGKRD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA221730

   5-{4-[1-(5-chlorothiophen-2-ylmethyl)-6-fluoro-1H-indol-3-yl]piperidin-1-ylmethyl}-2-methoxybenzoic 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: 513.03

Molecular Weight (Monoisotopic): 512.1337

AlogP: 6.63

#Rotatable Bonds: 7

Polar Surface Area: 54.70

Molecular Species: ZWITTERION

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.22

CX Basic pKa: 8.76

CX LogP: 3.83

CX LogD: 3.81

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -1.48

References

1. Fonquerna S, Miralpeix M, Pagès L, Puig C, Cardús A, Antón F, Cárdenas A, Vilella D, Aparici M, Calaf E, Prieto J, Gras J, Huerta JM, Warrellow G, Beleta J, Ryder H..  (2004)  Synthesis and structure-activity relationships of novel histamine H1 antagonists: indolylpiperidinyl benzoic acid derivatives.,  47  (25): [PMID:15566302] [10.1021/jm0498203]

Source

Source(1):

• Scientific Literature