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

ID: ALA2385901

Chembl Id: CHEMBL2385901

PubChem CID: 68503758

Max Phase: Preclinical

Molecular Formula: C25H21FN2O3

Molecular Weight: 416.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3cc(F)ccc31)CN(C(=O)Cc1cccc3ccccc13)CC2

Standard InChI:  InChI=1S/C25H21FN2O3/c26-18-8-9-22-20(13-18)21-14-27(11-10-23(21)28(22)15-25(30)31)24(29)12-17-6-3-5-16-4-1-2-7-19(16)17/h1-9,13H,10-12,14-15H2,(H,30,31)

Standard InChI Key:  OMXKUEXZCQUFSZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2385901

   2-[8-fluoro-2-(2-naphthalen-1-ylacetyl)-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: 416.45

Molecular Weight (Monoisotopic): 416.1536

AlogP: 4.15

#Rotatable Bonds: 4

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: 3.99

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 0.47

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -1.28

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