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

ID: ALA2385906

Chembl Id: CHEMBL2385906

PubChem CID: 11695689

Max Phase: Preclinical

Molecular Formula: C20H18N2O3

Molecular Weight: 334.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cn1c2c(c3ccccc31)CN(C(=O)c1ccccc1)CC2

Standard InChI:  InChI=1S/C20H18N2O3/c23-19(24)13-22-17-9-5-4-8-15(17)16-12-21(11-10-18(16)22)20(25)14-6-2-1-3-7-14/h1-9H,10-13H2,(H,23,24)

Standard InChI Key:  MTLOUGLEHWJVAT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2385906

   2-(2-benzoyl-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: 334.38

Molecular Weight (Monoisotopic): 334.1317

AlogP: 2.92

#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: 3.93

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: -0.67

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: -1.07

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]

2. Valdenaire A, Pothier J, Renneberg D, Riederer MA, Peter O, Leroy X, Gnerre C, Fretz H..  (2013)  Evolution of novel tricyclic CRTh2 receptor antagonists from a (E)-2-cyano-3-(1H-indol-3-yl)acrylamide scaffold.,  23  (4): [PMID:23324405] [10.1016/j.bmcl.2012.12.050]

Source

Source(1):

• Scientific Literature