SCS-C002258
1,8-Dihydroxy-6-methoxy-9,10-dioxo-9,10-dihydroanthracene-3-carboxylic acid
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Anthraquinones and anthrones
Chemical Structure
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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
Eurotium sp.
(gorgonian-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Eurotium
Species
NA
Xuwen
Study on the Secondary Metabolites of Two Fungi from the South China Sea.
Drug-likeness (Lipinski Ro5)
Molecular Weight
314.0 Da
Threshold ≤ 500
ALogP
1.58
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H10O7
Molecular Weight:
314.0000 Da
SMILES:
COc1cc(O)c2c(c1)C(=O)c1cc(C(=O)O)cc(O)c1C2=O
InChIKey:
HEULMVKOOVHXME-UHFFFAOYSA-N
InChI:
InChI=1S/C16H10O7/c1-23-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-6(16(21)22)3-10(12)17/h2-5,17-18H,1H3,(H,21,22)
Calculated Properties
ALogP:
1.580 lipophilicity
TPSA:
121.13 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
3
(2 aromatic)
Chiral Centers:
0
Fsp³:
0.0625 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002258
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Anthraquinones and anthrones
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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | α-glucosidase, DNA topoisomerase I | 0.1009 mM | — |
| Antiviral | inhibitory activity | influenza A virus A/Puerto Rico/8/34 (H1N1) | the known xanthones 14–16 exhibited broad inhibitory activities against three influenza A virus subtypes | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antibacterial | inhibitory activity | Methicillin-resistant Staphylococcus aureus; Staphylococcus aureus | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | inhibitory activity | K562; SGC-7901; A549; Hela cell lines | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |