2,3-difluorosialic acid; 5-N-(acetylamino)-2,3,5-trideoxy-2,3-difluoro-D-erythro-beta-L-manno-2-nonulopyranosonic acid

ID: ALA4128362

Chembl Id: CHEMBL4128362

PubChem CID: 91885381

Max Phase: Preclinical

Molecular Formula: C11H17F2NO8

Molecular Weight: 329.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H17F2NO8/c1-3(16)14-5-7(19)9(12)11(13,10(20)21)22-8(5)6(18)4(17)2-15/h4-9,15,17-19H,2H2,1H3,(H,14,16)(H,20,21)/t4-,5-,6-,7-,8-,9-,11-/m1/s1

Standard InChI Key:  HMALKZAXODOYOP-DAXAGCIGSA-N

Alternative Forms

1. Parent:

   

   ALA4128362

   (2r,3r,4r,5r,6r)-5-(Acetylamino)-2,3-Difluoro-4-Hydroxy-6-[(1r,2r)-1,2,3-Trihydroxypropyl]tetrahydro-2h-Pyran-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: 329.25

Molecular Weight (Monoisotopic): 329.0922

AlogP: -2.95

#Rotatable Bonds: 5

Polar Surface Area: 156.55

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.18

CX Basic pKa: ┄

CX LogP: -2.81

CX LogD: -6.26

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.31

Np Likeness Score: 0.94

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