(2R,3R,4S)-3-acetamido-2-((1R,2R)-1,2-dihydroxy-3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylate

ID: ALA1289650

Chembl Id: CHEMBL1289650

PubChem CID: 52948862

Max Phase: Preclinical

Molecular Formula: C14H20N4O8

Molecular Weight: 372.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)Cn2cc(CO)nn2)OC(C(=O)O)=C[C@@H]1O

Standard InChI:  InChI=1S/C14H20N4O8/c1-6(20)15-11-8(21)2-10(14(24)25)26-13(11)12(23)9(22)4-18-3-7(5-19)16-17-18/h2-3,8-9,11-13,19,21-23H,4-5H2,1H3,(H,15,20)(H,24,25)/t8-,9+,11+,12+,13+/m0/s1

Standard InChI Key:  IVIBRRKQZOQRAE-IINAIABHSA-N

Alternative Forms

1. Parent:

   

   ALA1289650

   (2R,3R,4S)-3-acetamido-2-((1R,2R)-1,2-dihydroxy-3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylate

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: 372.33

Molecular Weight (Monoisotopic): 372.1281

AlogP: -3.27

#Rotatable Bonds: 7

Polar Surface Area: 187.26

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.98

CX Basic pKa:

CX LogP: -3.84

CX LogD: -7.31

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 0.32

References

1. Zou Y, Albohy A, Sandbhor M, Cairo CW..  (2010)  Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.,  20  (24): [PMID:21036040] [10.1016/j.bmcl.2010.09.111]

2. Albohy A, Zhang Y, Smutova V, Pshezhetsky AV, Cairo CW..  (2013)  Identification of Selective Nanomolar Inhibitors of the Human Neuraminidase, NEU4.,  4  (6): [PMID:24900705] [10.1021/ml400080t]

3.  (2018)  Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data