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

ID: ALA3144460

Chembl Id: CHEMBL3144460

PubChem CID: 11431349

Max Phase: Preclinical

Molecular Formula: C17H15FN4O9S

Molecular Weight: 470.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COc3no[n+]([O-])c3S(=O)(=O)c3ccccc3)O2)cc1F

Standard InChI:  InChI=1S/C17H15FN4O9S/c18-10-7-21(17(25)19-14(10)24)13-6-11(23)12(30-13)8-29-15-16(22(26)31-20-15)32(27,28)9-4-2-1-3-5-9/h1-5,7,11-13,23H,6,8H2,(H,19,24,25)/t11-,12+,13+/m0/s1

Standard InChI Key:  XQXJUPSZSRJDSM-YNEHKIRRSA-N

Alternative Forms

1. Parent:

   

   ALA3144460

   1-[(2R,4S,5R)-5-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-fluoropyrimidine-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: 470.39

Molecular Weight (Monoisotopic): 470.0544

AlogP: -1.14

#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: 8.08

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.48

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: -0.33

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