SCS-C007175
2-hydroxy-1-(hydroxymethyl)-8-methoxy-3-methyl-9H-xanthen-9-one
Pathway: Polyketides
Superclass: Xanthones
Class: Methyl xanthones
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Aspergillus sydowii
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus sydowii
South China Sea
DOI:
10.1016/j.fitote.2019.03.031
· Fitoterapia
Drug-likeness (Lipinski Ro5)
Molecular Weight
286.3 Da
Threshold ≤ 500
ALogP
2.46
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H14O5
Molecular Weight:
286.2830 Da
SMILES:
COc1cccc2oc3cc(C)c(O)c(CO)c3c(=O)c12
InChIKey:
YRDJXNRZNOUOGI-UHFFFAOYSA-N
InChI:
InChI=1S/C16H14O5/c1-8-6-12-13(9(7-17)15(8)18)16(19)14-10(20-2)4-3-5-11(14)21-12/h3-6,17-18H,7H2,1-2H3
Calculated Properties
ALogP:
2.461 lipophilicity
TPSA:
79.90 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
3
(3 aromatic)
Chiral Centers:
0
Fsp³:
0.1875 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007175
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Xanthones
NPClassifier Class:
Methyl xanthones
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
Activity values are displayed only when a quantitative or clearly reported result is available.
Tested organisms, cell lines and molecular targets are shown under Target / model.
| Activity | Assay | Target / model | Result | Reference |
|---|---|---|---|---|
| Antiviral | inhibition | influenza A virus subtypes A/Puerto Rico/8/34 (H1N1) and A/FM-1/1/47 (H1N1) | 0.78–3.56 μM | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | inhibition | MDCK cells | > 200.0 μM | 10.1016/j.fitote.2019.03.031 Fitoterapia |