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

ID: ALA1289754

Chembl Id: CHEMBL1289754

PubChem CID: 52941156

Max Phase: Preclinical

Molecular Formula: C15H22N4O8

Molecular Weight: 386.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H22N4O8/c1-7(21)16-12-9(22)4-11(15(25)26)27-14(12)13(24)10(23)6-19-5-8(2-3-20)17-18-19/h4-5,9-10,12-14,20,22-24H,2-3,6H2,1H3,(H,16,21)(H,25,26)/t9-,10+,12+,13+,14+/m0/s1

Standard InChI Key:  LOBCLUJEPFNFNV-NRFQWKTPSA-N

Alternative Forms

1. Parent:

   

   ALA1289754

   (2R,3R,4S)-3-acetamido-2-((1R,2R)-1,2-dihydroxy-3-(4-(2-hydroxyethyl)-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: 386.36

Molecular Weight (Monoisotopic): 386.1438

AlogP: -3.23

#Rotatable Bonds: 8

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: 3.03

CX Basic pKa: 0.38

CX LogP: -3.60

CX LogD: -7.07

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: 0.30

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. Bourguet E, Figurska S, Fra Czek MM..  (2022)  Human Neuraminidases: Structures and Stereoselective Inhibitors.,  65  (4.0): [PMID:35170942] [10.1021/acs.jmedchem.1c01612]

Source

Source(1):

• Scientific Literature