SCS-C000833
6-epi-ophiobolin N
Pathway: Terpenoids
Superclass: Sesterterpenoids
Class: Ophiobolane sesterterpenoids
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 insuetus SD-512
(deep-sea fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus insuetus
South China Sea
· -1331m
DOI:
10.1021/acs.jnatprod.0c00860
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
368.6 Da
Threshold ≤ 500
ALogP
6.08
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C25H36O2
Molecular Weight:
368.6000 Da
SMILES:
CC(C)=CCC[C@H](C)[C@H]1CC[C@]2(C)C[C@@H]3C(C)=CC(=O)[C@H]3/C(C=O)=C\C[C@@H]12
InChIKey:
YHDCEAQTLJKEIK-PFQMJOEJSA-N
InChI:
InChI=1S/C25H36O2/c1-16(2)7-6-8-17(3)20-11-12-25(5)14-21-18(4)13-23(27)24(21)19(15-26)9-10-22(20)25/h7,9,13,15,17,20-22,24H,6,8,10-12,14H2,1-5H3/b19-9-/t17-,20+,21+,22-,24-,25+/m0/s1
Calculated Properties
ALogP:
6.082 lipophilicity
TPSA:
34.14 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
2
Rotatable Bonds:
5
Ring Count:
3
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.6800 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000833
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Ophiobolane sesterterpenoids
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 | GI50 | ACHN; PC-3; MDA-MB-231 cells | 0.2–0.3 μM | 10.1021/acs.jnatprod.0c00860 Journal of Natural Products |