ID: ALA489924

Max Phase: Preclinical

Molecular Formula: C25H28F7N3O3

Molecular Weight: 491.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)O.Cc1cc(F)ccc1[C@@H]1CNCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C23H24F7N3O.C2H4O2/c1-13-8-18(24)4-5-19(13)20-12-31-6-7-33(20)21(34)32(3)14(2)15-9-16(22(25,26)27)11-17(10-15)23(28,29)30;1-2(3)4/h4-5,8-11,14,20,31H,6-7,12H2,1-3H3;1H3,(H,3,4)/t14-,20+;/m1./s1

Standard InChI Key:  SOVDZYIWONLWDU-MRVNXENUSA-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: 491.45

Molecular Weight (Monoisotopic): 491.1808

AlogP: 5.93

#Rotatable Bonds: 3

Polar Surface Area: 35.58

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 7.45

CX LogP: 5.33

CX LogD: 5.01

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.54

Np Likeness Score: -1.01

References

1. Di Fabio R, Griffante C, Alvaro G, Pentassuglia G, Pizzi DA, Donati D, Rossi T, Guercio G, Mattioli M, Cimarosti Z, Marchioro C, Provera S, Zonzini L, Montanari D, Melotto S, Gerrard PA, Trist DG, Ratti E, Corsi M..  (2009)  Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor antagonist.,  52  (10): [PMID:19388677] [10.1021/jm900023b]

Source

Source(1):

• Scientific Literature