SCS-C000459
3,7-dihydroxy-1,9-dimethyl dibenzofuran
Pathway: Polyketides
Superclass: Aromatic polyketides
Class: Usnic acid and derivatives
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 versicolor
(coral-associated fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus versicolor
South China Sea
DOI:
10.3390/md23110429
· Marine Drugs
Talaromyces sp. SCSIO 041201
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Trichocomaceae
Genus
Talaromyces
Species
NA
South China Sea
DOI:
10.1080/14786419.2020.1836632
· Natural Product Research
Drug-likeness (Lipinski Ro5)
Molecular Weight
228.2 Da
Threshold ≤ 500
ALogP
3.61
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C14H12O3
Molecular Weight:
228.2470 Da
SMILES:
Cc1cc(O)cc2oc3cc(O)cc(C)c3c12
InChIKey:
SCSANHGJZDQFTD-UHFFFAOYSA-N
InChI:
InChI=1S/C14H12O3/c1-7-3-9(15)5-11-13(7)14-8(2)4-10(16)6-12(14)17-11/h3-6,15-16H,1-2H3
Calculated Properties
ALogP:
3.614 lipophilicity
TPSA:
53.60 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
3
(3 aromatic)
Chiral Centers:
0
Fsp³:
0.1429 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000459
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Aromatic polyketides
NPClassifier Class:
Usnic acid and derivatives
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 |
|---|---|---|---|---|
| Antifouling | LC50 | Bugula neritina larva | 3.06 μg/mL | 10.1080/14786419.2020.1836632 Natural Product Research |
| Antibacterial | MIC | E. coli, MRSA, S. aureus, E. faecalis | 0.45–15.6 μg/mL | 10.1080/14786419.2020.1836632 Natural Product Research |
| Anti-inflammatory | inhibitory activity | NF-κB (LPS-induced) | Compounds 6–8 exhibited inhibition of lipopolysaccharide (LPS)-induced NF-κB luciferase activities in RAW 264.7 macrophages at 20 μM | 10.3390/md23110429 Marine Drugs |
| Bone metabolism / Osteoclast | inhibitory activity | RANKL-induced osteoclast differentiation | Compound 6 could inhibit RANKL-induced osteoclast differentiation in bone marrow macrophage cells (BMMs) without visible evidence of cytotoxicity | 10.3390/md23110429 Marine Drugs |
| Anti-inflammatory | binding affinity | NF-κB p65 protein | -7.4 kcal/mol | 10.3390/md23110429 Marine Drugs |