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

ID: ALA2386072

Chembl Id: CHEMBL2386072

PubChem CID: 11631965

Max Phase: Preclinical

Molecular Formula: C21H20N2O4

Molecular Weight: 364.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c1c(n2CC(=O)O)CCN(C(=O)c2ccccc2)C1

Standard InChI:  InChI=1S/C21H20N2O4/c1-27-15-7-8-18-16(11-15)17-12-22(21(26)14-5-3-2-4-6-14)10-9-19(17)23(18)13-20(24)25/h2-8,11H,9-10,12-13H2,1H3,(H,24,25)

Standard InChI Key:  JCYDUAGFTWKEMN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2386072

   2-(2-benzoyl-8-methoxy-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: 364.40

Molecular Weight (Monoisotopic): 364.1423

AlogP: 2.93

#Rotatable Bonds: 4

Polar Surface Area: 71.77

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: -0.91

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.77

Np Likeness Score: -1.08

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