(2R,3R,5R,6R)-5-acetamido-2,3-difluoro-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid

ID: ALA4126987

Chembl Id: CHEMBL4126987

PubChem CID: 71726233

Max Phase: Preclinical

Molecular Formula: C11H17F2NO7

Molecular Weight: 313.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1C[C@@H](F)[C@](F)(C(=O)O)O[C@H]1[C@H](O)[C@H](O)CO

Standard InChI:  InChI=1S/C11H17F2NO7/c1-4(16)14-5-2-7(12)11(13,10(19)20)21-9(5)8(18)6(17)3-15/h5-9,15,17-18H,2-3H2,1H3,(H,14,16)(H,19,20)/t5-,6-,7-,8-,9-,11-/m1/s1

Standard InChI Key:  AHSNGFVNAWRJGS-WNBQUBFESA-N

Alternative Forms

1. Parent:

   

   ALA4126987

   (2R,3R,5R,6R)-5-acetamido-2,3-bis(fluoranyl)-6-[(1R,2R)-1,2,3-tris(oxidanyl)propyl]oxane-2-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: 313.25

Molecular Weight (Monoisotopic): 313.0973

AlogP: -1.92

#Rotatable Bonds: 5

Polar Surface Area: 136.32

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: -2.12

CX LogD: -5.56

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.40

Np Likeness Score: 0.89

References

1. McKimm-Breschkin JL, Barrett S, Pilling PA, Hader S, Watts AG, Streltsov VA..  (2018)  Structural and Functional Analysis of Anti-Influenza Activity of 4-, 7-, 8- and 9-Deoxygenated 2,3-Difluoro- N-acetylneuraminic Acid Derivatives.,  61  (5): [PMID:29397718] [10.1021/acs.jmedchem.7b01467]

Source

Source(1):

• Scientific Literature