1-((2R,3R,4S,5S)-5-((S)-1-(((2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-3-phenylprop-2-yn-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

ID: ALA5209278

Chembl Id: CHEMBL5209278

PubChem CID: 168295505

Max Phase: Preclinical

Molecular Formula: C22H25N3O9

Molecular Weight: 475.45

Names and Identifiers

Canonical SMILES:  NC[C@H]1O[C@@H](O[C@@H](C#Cc2ccccc2)[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C22H25N3O9/c23-10-13-15(27)18(30)21(33-13)32-12(7-6-11-4-2-1-3-5-11)19-16(28)17(29)20(34-19)25-9-8-14(26)24-22(25)31/h1-5,8-9,12-13,15-21,27-30H,10,23H2,(H,24,26,31)/t12-,13+,15+,16-,17+,18+,19+,20+,21+/m0/s1

Standard InChI Key:  JOBXKGJAAUCNDS-UHAWNKIKSA-N

Alternative Forms

1. Parent:

   

   ALA5209278

   ---

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: 475.45

Molecular Weight (Monoisotopic): 475.1591

AlogP: -3.00

#Rotatable Bonds: 5

Polar Surface Area: 189.49

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -1.69

CX LogD: -2.81

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: 1.03

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]

2. Okamoto K, Ishikawa A, Okawa R, Yamamoto K, Sato T, Yokota SI, Chiba K, Ichikawa S..  (2021)  Design, synthesis and biological evaluation of simplified analogues of MraY inhibitory natural product with rigid scaffold.,  55  [PMID:35016115] [10.1016/j.bmc.2021.116556]

Source

Source(1):

• Scientific Literature