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

ID: ALA2181810

Chembl Id: CHEMBL2181810

PubChem CID: 11689895

Max Phase: Preclinical

Molecular Formula: C21H17F3N2O3

Molecular Weight: 402.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H17F3N2O3/c22-21(23,24)14-6-7-17-15(10-14)16-11-25(20(29)13-4-2-1-3-5-13)9-8-18(16)26(17)12-19(27)28/h1-7,10H,8-9,11-12H2,(H,27,28)

Standard InChI Key:  ICSJJGLAKDSPMF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2181810

   2-[2-benzoyl-8-(trifluoromethyl)-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: 402.37

Molecular Weight (Monoisotopic): 402.1191

AlogP: 3.94

#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: 4.00

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 0.25

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: -1.36

References

1. Pettipher R, Whittaker M..  (2012)  Update on the development of antagonists of chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2). From lead optimization to clinical proof-of-concept in asthma and allergic rhinitis.,  55  (7): [PMID:22224640] [10.1021/jm2013997]

2. 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