SCS-C007153
eupenicisirenin C
Pathway: Terpenoids
Superclass: Sesquiterpenoids
Class: Cyclobisabolane sesquiterpenoids
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
Penicillium sp. SCSIO 41410
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
DOI:
10.1016/j.ejmech.2023.116068
· European Journal of Medicinal Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
238.3 Da
Threshold ≤ 500
ALogP
2.00
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C13H18O4
Molecular Weight:
238.2830 Da
SMILES:
COC(=O)CCC1(C)C2C=C(C(=O)O)CCC21
InChIKey:
FVAXAFUDRXJYBC-UHFFFAOYSA-N
InChI:
InChI=1S/C13H18O4/c1-13(6-5-11(14)17-2)9-4-3-8(12(15)16)7-10(9)13/h7,9-10H,3-6H2,1-2H3,(H,15,16)
Calculated Properties
ALogP:
1.997 lipophilicity
TPSA:
63.60 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
2
(0 aromatic)
Chiral Centers:
3
Fsp³:
0.6923 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007153
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
Cyclobisabolane sesquiterpenoids
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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | LPS-induced NF-κB activation | 14.5 μM | 10.1016/j.ejmech.2023.116068 European Journal of Medicinal Chemistry |
| Anti-inflammatory | inhibitory effect | cGAS/STING, TBK1, IRF3-5D induced IFN-β luciferase activation; IFN-β, CXCL10, TNF-α mRNA levels | 1 diminished cGAS/STING, TBK1, or IRF3-5D induced IFN-β luciferase activation with the concentrations of 1–30 μM | 10.1016/j.ejmech.2023.116068 European Journal of Medicinal Chemistry |
| Bone metabolism / Osteoclast | inhibitory effect | RANKL-induced osteoclast differentiation | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.ejmech.2023.116068 European Journal of Medicinal Chemistry |
| Bone metabolism / Osteoclast | therapeutic effect | Prednisolone-induced osteoporosis | 1 showed the significant inhibitory effect on RANKL-induced osteoclast differentiation... displayed the therapeutic potential on prednisolone-induced zebrafish osteoporosis. | 10.1016/j.ejmech.2023.116068 European Journal of Medicinal Chemistry |