4-(2-(3-(4-hydroxy-3-methoxyphenyl)acryloyloxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

ID: ALA2086817

Chembl Id: CHEMBL2086817

PubChem CID: 70695288

Max Phase: Preclinical

Molecular Formula: C20H18N2O9S

Molecular Weight: 462.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)OCCOc2no[n+]([O-])c2S(=O)(=O)c2ccccc2)ccc1O

Standard InChI:  InChI=1S/C20H18N2O9S/c1-28-17-13-14(7-9-16(17)23)8-10-18(24)29-11-12-30-19-20(22(25)31-21-19)32(26,27)15-5-3-2-4-6-15/h2-10,13,23H,11-12H2,1H3/b10-8+

Standard InChI Key:  LHGROPWCRJCPGZ-CSKARUKUSA-N

Alternative Forms

1. Parent:

   

   ALA2086817

   2-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

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: 462.44

Molecular Weight (Monoisotopic): 462.0733

AlogP: 1.49

#Rotatable Bonds: 9

Polar Surface Area: 152.10

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.87

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -0.36

References

1. Li W, Li N, Tang Y, Li B, Liu L, Zhang X, Fu H, Duan JA..  (2012)  Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.,  22  (19): [PMID:22954735] [10.1016/j.bmcl.2012.08.038]

2. Xie Y, Yang Y, Li S, Xu Y, Lu W, Chen Z, Yang G, Li Y, Cao Y, Bian X..  (2017)  Phenylsulfonylfuroxan NO-donor phenols: Synthesis and multifunctional activities evaluation.,  25  (16): [PMID:28651914] [10.1016/j.bmc.2017.06.023]

Source

Source(1):

• Scientific Literature