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SCS-C007176

2-hydroxy-1-(hydroxymethyl)-7,8-dimethoxy-3-methyl-9H-xanthen-9-one

Pathway: Polyketides Superclass: Xanthones Class: Methyl xanthones
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Chemical Structure

Structure of 2-hydroxy-1-(hydroxymethyl)-7,8-dimethoxy-3-methyl-9H-xanthen-9-one
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

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
316.3 Da
Threshold ≤ 500
ALogP
2.47
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C17H16O6
Molecular Weight:
316.3090 Da
SMILES:
COc1ccc2oc3cc(C)c(O)c(CO)c3c(=O)c2c1OC
InChIKey:
CLHDFKDJTJWRBE-UHFFFAOYSA-N
InChI:
InChI=1S/C17H16O6/c1-8-6-12-13(9(7-18)15(8)19)16(20)14-10(23-12)4-5-11(21-2)17(14)22-3/h4-6,18-19H,7H2,1-3H3
Calculated Properties
ALogP:
2.470 lipophilicity
TPSA:
89.13 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
6
Rotatable Bonds:
3
Ring Count:
3 (3 aromatic)
Chiral Centers:
0
Fsp³:
0.2353 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007176
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Xanthones
NPClassifier Class:
Methyl xanthones
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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
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Structure enlarged