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

ID: ALA2385899

Chembl Id: CHEMBL2385899

PubChem CID: 71733909

Max Phase: Preclinical

Molecular Formula: C25H19F3N2O3

Molecular Weight: 452.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H19F3N2O3/c26-25(27,28)16-8-9-21-19(12-16)20-13-29(11-10-22(20)30(21)14-23(31)32)24(33)18-7-3-5-15-4-1-2-6-17(15)18/h1-9,12H,10-11,13-14H2,(H,31,32)

Standard InChI Key:  DFVBLFJUHBOAGA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2385899

   2-[2-(naphthalene-1-carbonyl)-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: 452.43

Molecular Weight (Monoisotopic): 452.1348

AlogP: 5.10

#Rotatable Bonds: 3

Polar Surface Area: 62.54

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.10

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 1.29

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.47

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