ID: ALA1215863

Max Phase: Preclinical

Molecular Formula: C21H15ClF3NO3

Molecular Weight: 421.80

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1c(O)c(C2(c3ccc(Cl)cc3)CCC2)nc2c(C(F)(F)F)cccc12

Standard InChI:  InChI=1S/C21H15ClF3NO3/c22-12-7-5-11(6-8-12)20(9-2-10-20)18-17(27)15(19(28)29)13-3-1-4-14(16(13)26-18)21(23,24)25/h1,3-8,27H,2,9-10H2,(H,28,29)

Standard InChI Key:  MLVASRCEOCFBAD-UHFFFAOYSA-N

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

Properties

Molecular Weight: 421.80

Molecular Weight (Monoisotopic): 421.0693

AlogP: 5.78

#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: 6.66

CX LogD: 3.24

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -0.27

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