SCS-C008295
sinunanolobatone A
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Cembrane diterpenoids
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
Sinularia nanolobata
(soft coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Sinulariidae
Genus
Sinularia
Species
Sinularia nanolobata
South China Sea
DOI:
10.1021/acs.orglett.1c02772
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
286.5 Da
Threshold ≤ 500
ALogP
5.77
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
1
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C20H30O
Molecular Weight:
286.4590 Da
SMILES:
C/C1=C\CC/C(C)=C/[C@H]2C[C@]2(C)C(=O)CC/C(C)=C/CC1
InChIKey:
YEBRVYUVRHAICK-AFFXFOQRSA-N
InChI:
InChI=1S/C20H30O/c1-15-7-5-9-16(2)11-12-19(21)20(4)14-18(20)13-17(3)10-6-8-15/h8-9,13,18H,5-7,10-12,14H2,1-4H3/b15-8+,16-9+,17-13+/t18-,20-/m0/s1
Calculated Properties
ALogP:
5.775 lipophilicity
TPSA:
17.07 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
1
Rotatable Bonds:
0
Ring Count:
2
(0 aromatic)
Chiral Centers:
2
Fsp³:
0.6500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008295
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Cembrane 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 |
|---|---|---|---|---|
| Anti-inflammatory | NO production inhibition | NO production | compounds 1, 2a, 3, 3a, 4, 5, 7, and 8 at 20 μM displayed inhibitory activity on NO production against LPS-induced inflammation-related BV-2 microglial cells | 10.1021/acs.orglett.1c02772 Organic Letters |
| Anti-inflammatory | pro-inflammatory cytokine mRNA level reduction | IL-6 mRNA | 10.0 μM | 10.1021/acs.orglett.1c02772 Organic Letters |
| Anti-inflammatory | pro-inflammatory cytokine mRNA level reduction | IL-1β mRNA | 20.0 μM | 10.1021/acs.orglett.1c02772 Organic Letters |