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

ID: ALA2386066

Chembl Id: CHEMBL2386066

PubChem CID: 11675066

Max Phase: Preclinical

Molecular Formula: C20H17ClN2O3

Molecular Weight: 368.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3cc(Cl)ccc31)CN(C(=O)c1ccccc1)CC2

Standard InChI:  InChI=1S/C20H17ClN2O3/c21-14-6-7-17-15(10-14)16-11-22(20(26)13-4-2-1-3-5-13)9-8-18(16)23(17)12-19(24)25/h1-7,10H,8-9,11-12H2,(H,24,25)

Standard InChI Key:  GMSNGAAHZCRDTP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2386066

   2-(2-benzoyl-8-chloro-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: 368.82

Molecular Weight (Monoisotopic): 368.0928

AlogP: 3.58

#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: 3.80

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: -0.13

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.36

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