(2R,3R,4R,5R,6R)-methyl 5-acetamido-4-amino-6-((1R,2R)-1,2-dihydroxy-3-(octyloxycarbonyloxy)propyl)-2,3-difluorotetrahydro-2H-pyran-2-carboxylate

ID: ALA3426116

Chembl Id: CHEMBL3426116

PubChem CID: 118736935

Max Phase: Preclinical

Molecular Formula: C21H36F2N2O9

Molecular Weight: 498.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCOC(=O)OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](F)(C(=O)OC)[C@H](F)[C@H](N)[C@H]1NC(C)=O

Standard InChI:  InChI=1S/C21H36F2N2O9/c1-4-5-6-7-8-9-10-32-20(30)33-11-13(27)16(28)17-15(25-12(2)26)14(24)18(22)21(23,34-17)19(29)31-3/h13-18,27-28H,4-11,24H2,1-3H3,(H,25,26)/t13-,14-,15-,16-,17-,18-,21-/m1/s1

Standard InChI Key:  OQRDNOBXBWGLQO-VAMIYIBTSA-N

Alternative Forms

1. Parent:

   

   ALA3426116

   ---

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: 498.52

Molecular Weight (Monoisotopic): 498.2389

AlogP: 0.63

#Rotatable Bonds: 13

Polar Surface Area: 166.64

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.67

CX Basic pKa: 7.67

CX LogP: 1.39

CX LogD: 0.93

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 0.66

References

1. Arns S, Tan J, Sun S, Galey A, Zisman N, Ross F, Udechukwu J, Dercho S, Gusti V, Paquette J, Webb M, Bourque E, Withers SG, Liggins R..  (2015)  Assessing the oral bioavailability of difluorosialic acid prodrugs, potent viral neuraminidase inhibitors, using a snapshot PK screening assay.,  25  (12): [PMID:25980910] [10.1016/j.bmcl.2015.04.059]

Source

Source(1):

• Scientific Literature