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

ID: ALA2386080

Chembl Id: CHEMBL2386080

PubChem CID: 68505327

Max Phase: Preclinical

Molecular Formula: C24H19ClN2O3

Molecular Weight: 418.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3cc(Cl)ccc31)CN(C(=O)c1cccc3ccccc13)CC2

Standard InChI:  InChI=1S/C24H19ClN2O3/c25-16-8-9-21-19(12-16)20-13-26(11-10-22(20)27(21)14-23(28)29)24(30)18-7-3-5-15-4-1-2-6-17(15)18/h1-9,12H,10-11,13-14H2,(H,28,29)

Standard InChI Key:  ULKXLZPONKIBOQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2386080

   2-[8-chloro-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: 418.88

Molecular Weight (Monoisotopic): 418.1084

AlogP: 4.73

#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: 3.92

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 0.92

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.30

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