ID: ALA459695

Max Phase: Preclinical

Molecular Formula: C13H8O4

Molecular Weight: 228.20

Molecule Type: Small molecule

Representations

Synonyms (1): 1,6-Dihydroxyxanthone
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1c2ccc(O)cc2oc2cccc(O)c12

Standard InChI:  InChI=1S/C13H8O4/c14-7-4-5-8-11(6-7)17-10-3-1-2-9(15)12(10)13(8)16/h1-6,14-15H

Standard InChI Key:  IUSXGFFUHTXSRD-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 228.20

Molecular Weight (Monoisotopic): 228.0423

AlogP: 2.36

#Rotatable Bonds: 0

Polar Surface Area: 70.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.40

CX Basic pKa:

CX LogP: 3.00

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 17

QED Weighted: 0.58

Np Likeness Score: 1.18

References

1. Liu Y, Ke Z, Cui J, Chen WH, Ma L, Wang B..  (2008)  Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as alpha-glucosidase inhibitors.,  16  (15): [PMID:18632275] [10.1016/j.bmc.2008.06.043]

2. Verbanac D, Jain SC, Jain N, Chand M, Cipčić Paljetak H, Matijašić M, Perić M, Stepanić V, Saso L..  (2012)  An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.,  20  (10): [PMID:22537683] [10.1016/j.bmc.2012.03.074]

3. Shi TX, Wang S, Zeng KW, Tu PF, Jiang Y..  (2013)  Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells.,  23  (21): [PMID:24042007] [10.1016/j.bmcl.2013.08.085]

4. Dibwe DF, Awale S, Kadota S, Morita H, Tezuka Y..  (2013)  Heptaoxygenated xanthones as anti-austerity agents from Securidaca longepedunculata.,  21  (24): [PMID:24216090] [10.1016/j.bmc.2013.10.027]

5. Klein-Júnior LC, Corrêa R, Vander Heyden Y, Cechinel Filho V..  (2019)  All that glitters is not gold: Panning cytotoxic natural products and derivatives with a fused tricyclic backbone by the estimation of their leadlikeness for cancer treatment.,  166  [PMID:30684866] [10.1016/j.ejmech.2019.01.028]

6. Dean B, Cooper G, Shivkumar M, Snape TJ..  (2023)  Hydroxy-xanthones as promising antiviral agents: Synthesis and biological evaluation against human coronavirus OC43.,  84  [PMID:36863494] [10.1016/j.bmcl.2023.129211]

Source

Source(1):

• Scientific Literature