2-(1-(4-Chlorophenyl)cyclopropyl)-3-hydroxy-8-(trifluoromethyl)-quinoline-4-carboxylic Acid

ID: ALA1215851

Chembl Id: CHEMBL1215851

Cas Number: 1067186-56-4

PubChem CID: 25102990

Max Phase: Preclinical

Molecular Formula: C20H13ClF3NO3

Molecular Weight: 407.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(O)c(C2(c3ccc(Cl)cc3)CC2)nc2c(C(F)(F)F)cccc12

Standard InChI:  InChI=1S/C20H13ClF3NO3/c21-11-6-4-10(5-7-11)19(8-9-19)17-16(26)14(18(27)28)12-2-1-3-13(15(12)25-17)20(22,23)24/h1-7,26H,8-9H2,(H,27,28)

Standard InChI Key:  RACDNEQBIMTJPQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1215851

   2-(1-(4-Chlorophenyl)cyclopropyl)-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic 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: 407.77

Molecular Weight (Monoisotopic): 407.0536

AlogP: 5.39

#Rotatable Bonds: 3

Polar Surface Area: 70.42

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.31

CX Basic pKa: 0.28

CX LogP: 6.22

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.28

References

1. Huang A, Moretto A, Janz K, Lowe M, Bedard PW, Tam S, Di L, Clerin V, Sushkova N, Tchernychev B, Tsao DH, Keith JC, Shaw GD, Schaub RG, Wang Q, Kaila N..  (2010)  Discovery of 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury.,  53  (16): [PMID:20718494] [10.1021/jm9013696]

Source

Source(1):

• Scientific Literature