2-[(3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindol-2-yl]-1,3-oxazol-4(5H)-one

ID: ALA2402572

Max Phase: Preclinical

Molecular Formula: C28H28F6N2O4

Molecular Weight: 570.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1[C@H]1[C@@H]2CN(C3=NC(=O)CO3)C[C@H]2CC[C@@H]1O[C@H](CO)c1cc(C(F)(F)F)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C28H28F6N2O4/c1-15-4-2-3-5-20(15)25-21-12-36(26-35-24(38)14-39-26)11-16(21)6-7-22(25)40-23(13-37)17-8-18(27(29,30)31)10-19(9-17)28(32,33)34/h2-5,8-10,16,21-23,25,37H,6-7,11-14H2,1H3/t16-,21-,22+,23-,25+/m1/s1

Standard InChI Key:  VBUOSAKACWCALS-IOOJMYGHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2402572

   ---

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: 570.53

Molecular Weight (Monoisotopic): 570.1953

AlogP: 5.49

#Rotatable Bonds: 5

Polar Surface Area: 71.36

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.11

CX Basic pKa: ┄

CX LogP: 5.08

CX LogD: 4.73

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.48

Np Likeness Score: 0.08

References

1. Kassick AJ, Jiang J, Bunda J, Wilson D, Bao J, Lu H, Lin P, Ball RG, Doss GA, Tong X, Tsao KL, Wang H, Chicchi G, Karanam B, Tschirret-Guth R, Samuel K, Hora DF, Kumar S, Madeira M, Eng W, Hargreaves R, Purcell M, Gantert L, Cook J, DeVita RJ, Mills SG..  (2013)  2-[(3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindol-2-yl]-1,3-oxazol-4(5H)-one: a potent human NK1 receptor antagonist with multiple clearance pathways.,  56  (14): [PMID:23808489] [10.1021/jm400751p]

Source

Source(1):

• Scientific Literature