1-[5-(4-Benzenesulfonyl-5-oxy-furazan-3-yloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

ID: ALA3144455

Chembl Id: CHEMBL3144455

PubChem CID: 11487797

Max Phase: Preclinical

Molecular Formula: C17H16N4O9S

Molecular Weight: 452.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@H]2C[C@H](O)[C@@H](COc3no[n+]([O-])c3S(=O)(=O)c3ccccc3)O2)c(=O)[nH]1

Standard InChI:  InChI=1S/C17H16N4O9S/c22-11-8-14(20-7-6-13(23)18-17(20)24)29-12(11)9-28-15-16(21(25)30-19-15)31(26,27)10-4-2-1-3-5-10/h1-7,11-12,14,22H,8-9H2,(H,18,23,24)/t11-,12+,14+/m0/s1

Standard InChI Key:  FHOSMOKEYPJCQK-OUCADQQQSA-N

Alternative Forms

1. Parent:

   

   ALA3144455

   1-[(2R,4S,5R)-5-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxymethyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione

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: 452.40

Molecular Weight (Monoisotopic): 452.0638

AlogP: -1.28

#Rotatable Bonds: 6

Polar Surface Area: 180.66

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.71

CX Basic pKa: ┄

CX LogP: -0.74

CX LogD: -0.74

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.07

References

1. Moharram S, Zhou A, Wiebe LI, Knaus EE..  (2004)  Design and synthesis of 3'- and 5'-O-(3-benzenesulfonylfuroxan-4-yl)-2'-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents.,  47  (7): [PMID:15027876] [10.1021/jm030544m]

Source

Source(1):

• Scientific Literature