(2R,3R,4S)-3-acetamido-2-((1R,2R)-3-azido-1,2-dihydroxypropyl)-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylate

ID: ALA1289311

Chembl Id: CHEMBL1289311

PubChem CID: 15087872

Max Phase: Preclinical

Molecular Formula: C11H16N4O7

Molecular Weight: 316.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CN=[N+]=[N-])OC(C(=O)O)=C[C@@H]1O

Standard InChI:  InChI=1S/C11H16N4O7/c1-4(16)14-8-5(17)2-7(11(20)21)22-10(8)9(19)6(18)3-13-15-12/h2,5-6,8-10,17-19H,3H2,1H3,(H,14,16)(H,20,21)/t5-,6+,8+,9+,10+/m0/s1

Standard InChI Key:  ALVXTNDDVFJVAI-UFGQHTETSA-N

Alternative Forms

1. Parent:

   

   ALA1289311

   (2R,3R,4S)-3-acetamido-2-((1R,2R)-3-azido-1,2-dihydroxypropyl)-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: 316.27

Molecular Weight (Monoisotopic): 316.1019

AlogP: -1.75

#Rotatable Bonds: 6

Polar Surface Area: 185.08

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.12

CX Basic pKa:

CX LogP: -2.87

CX LogD: -6.44

Aromatic Rings: 0

Heavy Atoms: 22

QED Weighted: 0.22

Np Likeness Score: 1.24

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. Slack TJ, Li W, Shi D, McArthur JB, Zhao G, Li Y, Xiao A, Khedri Z, Yu H, Liu Y, Chen X..  (2018)  Triazole-linked transition state analogs as selective inhibitors against V. cholerae sialidase.,  26  (21): [PMID:30389408] [10.1016/j.bmc.2018.10.028]

Source

Source(1):

• Scientific Literature