(4S,5R,6R)-5-acetamido-4-(4-phenyl-1H-1,2,3-triazol-1-yl)-6-((1R,2R)-1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

ID: ALA213310

Chembl Id: CHEMBL213310

PubChem CID: 44416450

Max Phase: Preclinical

Molecular Formula: C19H22N4O7

Molecular Weight: 418.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1n1cc(-c2ccccc2)nn1

Standard InChI:  InChI=1S/C19H22N4O7/c1-10(25)20-16-13(23-8-12(21-22-23)11-5-3-2-4-6-11)7-15(19(28)29)30-18(16)17(27)14(26)9-24/h2-8,13-14,16-18,24,26-27H,9H2,1H3,(H,20,25)(H,28,29)/t13-,14+,16+,17+,18+/m0/s1

Standard InChI Key:  SDEQKRZVSOWXBW-QBBQCFRVSA-N

Alternative Forms

1. Parent:

   

   ALA213310

   (2R,3R,4S)-3-acetamido-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-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: 418.41

Molecular Weight (Monoisotopic): 418.1488

AlogP: -0.93

#Rotatable Bonds: 7

Polar Surface Area: 167.03

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.32

CX Basic pKa: ┄

CX LogP: -1.12

CX LogD: -4.54

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: 0.08

References

1. Li J, Zheng M, Tang W, He PL, Zhu W, Li T, Zuo JP, Liu H, Jiang H..  (2006)  Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities.,  16  (19): [PMID:16876409] [10.1016/j.bmcl.2006.07.047]

2. El-Deeb IM, Guillon P, Dirr L, von Itzstein M..  (2017)  Exploring inhibitor structural features required to engage the 216-loop of human parainfluenza virus type-3 hemagglutinin-neuraminidase.,  8  (1): [PMID:30108698] [10.1039/C6MD00519E]

Source

Source(1):

• Scientific Literature