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

ID: ALA2386071

Chembl Id: CHEMBL2386071

PubChem CID: 71733817

Max Phase: Preclinical

Molecular Formula: C20H16F2N2O3

Molecular Weight: 370.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3cc(F)cc(F)c31)CN(C(=O)c1ccccc1)CC2

Standard InChI:  InChI=1S/C20H16F2N2O3/c21-13-8-14-15-10-23(20(27)12-4-2-1-3-5-12)7-6-17(15)24(11-18(25)26)19(14)16(22)9-13/h1-5,8-9H,6-7,10-11H2,(H,25,26)

Standard InChI Key:  BTLHJJZUGWLEBW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2386071

   2-(2-benzoyl-6,8-difluoro-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: 370.36

Molecular Weight (Monoisotopic): 370.1129

AlogP: 3.20

#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: 3.73

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: -0.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.77

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