SCS-C006063
21-hydroxyterpestacin
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Cembrane diterpenoids | Dolabellane diterpenoids
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
Arthrinium sp. SCSIO 41221
(sponge-derived fungus)
Original source name: Arthrinium sp. SCSIO41221
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Apiosporaceae
Genus
Arthrinium
Species
NA
Offshore Hainan Island
· 18°13'50.2"N, 109°37'15.8"E
DOI:
10.3390/molecules28217246
· Molecules
Drug-likeness (Lipinski Ro5)
Molecular Weight
418.6 Da
Threshold ≤ 500
ALogP
4.16
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C25H38O5
Molecular Weight:
418.5740 Da
SMILES:
C/C1=C\C[C@]2(C)C(=O)C(O)=C([C@H](C)CO)[C@H]2C/C=C(\C)[C@@H](O)CC/C(CO)=C/CC1
InChIKey:
FWMNQZFMPSHEAG-LCUMIZEYSA-N
InChI:
InChI=1S/C25H38O5/c1-16-6-5-7-19(15-27)9-11-21(28)17(2)8-10-20-22(18(3)14-26)23(29)24(30)25(20,4)13-12-16/h7-8,12,18,20-21,26-29H,5-6,9-11,13-15H2,1-4H3/b16-12+,17-8+,19-7-/t18-,20-,21+,25+/m1/s1
Calculated Properties
ALogP:
4.159 lipophilicity
TPSA:
97.99 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
2
(0 aromatic)
Chiral Centers:
4
Fsp³:
0.6400 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006063
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Cembrane diterpenoids
Dolabellane diterpenoids
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 |
|---|---|---|---|---|
| Antitumor | — | human cancer cells MDAMB-231 | All of the compounds were evaluated for their cytotoxic activities against the human cancer cells MDAMB-231, C4-2B, MGC803, MDA-MB-468, and A549 using the CCK-8 method, but they exhibited no inhibitory activities at 5 μM. | 10.3390/molecules28217246 Molecules |
| Antitumor | — | U87MG-derived glioblastoma stem cells (GSCs) | compounds 2 and 5 were found to show weak inhibitory effects against U87MG-derived GSCs. | 10.3390/molecules28217246 Molecules |
| Receptor / Signaling modulation | — | HIF-1α and CD133 protein | Compared to terpestacin and the positive control 4-200, compound 5 showed stronger activity (Figure S26). | 10.3390/molecules28217246 Molecules |