2-(6-Chloro-2-(3-chlorobenzoyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid

ID: ALA2386078

Chembl Id: CHEMBL2386078

PubChem CID: 71733818

Max Phase: Preclinical

Molecular Formula: C20H15Cl2FN2O3

Molecular Weight: 421.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3cc(F)cc(Cl)c31)CN(C(=O)c1cccc(Cl)c1)CC2

Standard InChI:  InChI=1S/C20H15Cl2FN2O3/c21-12-3-1-2-11(6-12)20(28)24-5-4-17-15(9-24)14-7-13(23)8-16(22)19(14)25(17)10-18(26)27/h1-3,6-8H,4-5,9-10H2,(H,26,27)

Standard InChI Key:  PVCHZSUUQQWRNF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2386078

   2-[6-chloro-2-(3-chlorobenzoyl)-8-fluoro-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: 421.25

Molecular Weight (Monoisotopic): 420.0444

AlogP: 4.37

#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: 3.66

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 0.56

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.57

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