ID: ALA538661

Max Phase: Preclinical

Molecular Formula: C20H18O8

Molecular Weight: 386.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)/C=C/c1cc(O)c2c(c1)[C@@H](C(=O)OC)[C@H](c1ccc(O)c(O)c1)O2

Standard InChI:  InChI=1S/C20H18O8/c1-26-16(24)6-3-10-7-12-17(20(25)27-2)18(28-19(12)15(23)8-10)11-4-5-13(21)14(22)9-11/h3-9,17-18,21-23H,1-2H3/b6-3+/t17-,18+/m1/s1

Standard InChI Key:  HDONJQIYHGHIJV-VCPQXCNPSA-N

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

Properties

Molecular Weight: 386.36

Molecular Weight (Monoisotopic): 386.1002

AlogP: 2.38

#Rotatable Bonds: 4

Polar Surface Area: 122.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.08

CX Basic pKa:

CX LogP: 2.80

CX LogD: 2.79

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: 1.53

References

1. Pieters L, Van Dyck S, Gao M, Bai R, Hamel E, Vlietinck A, Lemière G..  (1999)  Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization.,  42  (26): [PMID:10639289] [10.1021/jm990251m]

2. Apers S, Paper D, Bürgermeister J, Baronikova S, Van Dyck S, Lemière G, Vlietinck A, Pieters L..  (2002)  Antiangiogenic activity of synthetic dihydrobenzofuran lignans.,  65  (5): [PMID:12027748] [10.1021/np0103968]

3. Di Micco S, Spatafora C, Cardullo N, Riccio R, Fischer K, Pergola C, Koeberle A, Werz O, Chalal M, Vervandier-Fasseur D, Tringali C, Bifulco G..  (2016)  2,3-Dihydrobenzofuran privileged structures as new bioinspired lead compounds for the design of mPGES-1 inhibitors.,  24  (4): [PMID:26777299] [10.1016/j.bmc.2016.01.002]

Source

Source(1):

• Scientific Literature