SCS-C000852
sterigmatocystin
Pathway: Polyketides
Superclass: Chromanes | Xanthones
Class: Aflatoxins | 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 nidulans SD-531
(deep-sea fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus nidulans
South China Sea
DOI:
10.1007/s00343-020-0052-3
· Journal of Oceanology and Limnology
Drug-likeness (Lipinski Ro5)
Molecular Weight
324.3 Da
Threshold ≤ 500
ALogP
3.01
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C18H12O6
Molecular Weight:
324.3000 Da
SMILES:
COc1cc2c(c3oc4cccc(O)c4c(=O)c13)[C@@H]1C=CO[C@@H]1O2
InChIKey:
UTSVPXMQSFGQTM-DCXZOGHSSA-N
InChI:
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
Calculated Properties
ALogP:
3.006 lipophilicity
TPSA:
78.13 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
6
Rotatable Bonds:
1
Ring Count:
5
(3 aromatic)
Chiral Centers:
2
Fsp³:
0.1667 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000852
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Chromanes
Xanthones
NPClassifier Class:
Aflatoxins
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 |
|---|---|---|---|---|
| Antibacterial | MIC | Pseudomonas aeruginosa | 125.0 μg/mL | 10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology |
| Antitumor | IC50 | HepG2 | 12.5 ± 0.89 μM | 10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology |
| Antitumor | IC50 | Hela | 11.5 ± 0.99 μM | 10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology |
| Antitumor | IC50 | MCF-7 | 6.76 ± 0.31 μM | 10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology |
| Antitumor | IC50 | HT-29 cells | 8.16 ± 0.39 μM | 10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology |