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

ID: ALA5191710

Chembl Id: CHEMBL5191710

PubChem CID: 168287884

Max Phase: Preclinical

Molecular Formula: C23H25N3O9

Molecular Weight: 487.47

Names and Identifiers

Canonical SMILES:  NC[C@H]1O[C@@H](O[C@@H](C#Cc2ccccc2)[C@@]23CO[C@@H]([C@H](n4ccc(=O)[nH]c4=O)O2)[C@@H]3O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C23H25N3O9/c24-10-13-16(28)17(29)21(33-13)34-14(7-6-12-4-2-1-3-5-12)23-11-32-18(19(23)30)20(35-23)26-9-8-15(27)25-22(26)31/h1-5,8-9,13-14,16-21,28-30H,10-11,24H2,(H,25,27,31)/t13-,14+,16-,17-,18-,19+,20-,21+,23-/m1/s1

Standard InChI Key:  QEQDJQYUACSIQL-ULOMPZFWSA-N

Alternative Forms

1. Parent:

   

   ALA5191710

   ---

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: 487.47

Molecular Weight (Monoisotopic): 487.1591

AlogP: -2.59

#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: -1.30

CX LogD: -2.41

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: 1.13

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