(1S,3R,4R,7S)-1-[1-(S)-(5-Amino-5-deoxy-beta-D-ribofuranosyloxy)prop-2-yn-1-yl]-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

ID: ALA5200223

Chembl Id: CHEMBL5200223

PubChem CID: 168291525

Max Phase: Preclinical

Molecular Formula: C17H21N3O9

Molecular Weight: 411.37

Names and Identifiers

Canonical SMILES:  C#C[C@H](O[C@@H]1O[C@H](CN)[C@@H](O)[C@H]1O)[C@@]12CO[C@@H]([C@H](n3ccc(=O)[nH]c3=O)O1)[C@@H]2O

Standard InChI:  InChI=1S/C17H21N3O9/c1-2-8(28-15-11(23)10(22)7(5-18)27-15)17-6-26-12(13(17)24)14(29-17)20-4-3-9(21)19-16(20)25/h1,3-4,7-8,10-15,22-24H,5-6,18H2,(H,19,21,25)/t7-,8+,10-,11-,12-,13+,14-,15+,17-/m1/s1

Standard InChI Key:  YRXKVYWCKBPJQK-RODCLFSISA-N

Alternative Forms

1. Parent:

   

   ALA5200223

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.37

Molecular Weight (Monoisotopic): 411.1278

AlogP: -4.01

#Rotatable Bonds: 5

Polar Surface Area: 178.49

Molecular Species: BASE

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -3.27

CX LogD: -4.38

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: 1.53

References

1. Kusaka S, Yamamoto K, Shinohara M, Minato Y, Ichikawa S..  (2022)  Design, synthesis and conformation-activity relationship analysis of LNA/BNA-type 5'-O-aminoribosyluridine as MraY inhibitors.,  65  [PMID:35500521] [10.1016/j.bmc.2022.116744]

Source

Source(1):

• Scientific Literature