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

ID: ALA3144457

Chembl Id: CHEMBL3144457

PubChem CID: 11155544

Max Phase: Preclinical

Molecular Formula: C18H18N4O9S

Molecular Weight: 466.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](Oc3no[n+]([O-])c3S(=O)(=O)c3ccccc3)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C18H18N4O9S/c1-10-8-21(18(25)19-15(10)24)14-7-12(13(9-23)29-14)30-16-17(22(26)31-20-16)32(27,28)11-5-3-2-4-6-11/h2-6,8,12-14,23H,7,9H2,1H3,(H,19,24,25)/t12-,13+,14+/m0/s1

Standard InChI Key:  YMDLSHZOALFOFD-BFHYXJOUSA-N

Alternative Forms

1. Parent:

   

   ALA3144457

   1-[(2R,4S,5R)-4-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-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: 466.43

Molecular Weight (Monoisotopic): 466.0794

AlogP: -0.97

#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: 9.96

CX Basic pKa: ┄

CX LogP: -0.46

CX LogD: -0.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.16

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