2-(2-(1-Naphthoyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid

ID: ALA2385898

Chembl Id: CHEMBL2385898

PubChem CID: 68508048

Max Phase: Preclinical

Molecular Formula: C25H22N2O3

Molecular Weight: 398.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)c1c(n2CC(=O)O)CCN(C(=O)c2cccc3ccccc23)C1

Standard InChI:  InChI=1S/C25H22N2O3/c1-16-9-10-22-20(13-16)21-14-26(12-11-23(21)27(22)15-24(28)29)25(30)19-8-4-6-17-5-2-3-7-18(17)19/h2-10,13H,11-12,14-15H2,1H3,(H,28,29)

Standard InChI Key:  GEZZLXQCQXBMNF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2385898

   2-[8-methyl-2-(naphthalene-1-carbonyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl]acetic 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: 398.46

Molecular Weight (Monoisotopic): 398.1630

AlogP: 4.39

#Rotatable Bonds: 3

Polar Surface Area: 62.54

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.12

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 0.95

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -1.18

References

1. Fretz H, Valdenaire A, Pothier J, Hilpert K, Gnerre C, Peter O, Leroy X, Riederer MA..  (2013)  Identification of 2-(2-(1-naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid (setipiprant/ACT-129968), a potent, selective, and orally bioavailable chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2) antagonist.,  56  (12): [PMID:23721423] [10.1021/jm400122f]

Source

Source(1):

• Scientific Literature