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  3. [(1R,3S,5S,8E,12R,13R)-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.03,5]octadec-8-en-12-yl] acetate

SCS-C007656

[(1R,3S,5S,8E,12R,13R)-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.03,5]octadec-8-en-12-yl] acetate

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids
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Chemical Structure

Structure of [(1R,3S,5S,8E,12R,13R)-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.03,5]octadec-8-en-12-yl] acetate
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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.
Download: SDF SMILES

Source Information

Sinularia pedunculata (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia pedunculata
South China Sea
DOI: 10.1002/cbdv.202401146  · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight
376.5 Da
Threshold ≤ 500
ALogP
4.25
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C22H32O5
Molecular Weight:
376.4930 Da
SMILES:
C=C1C(=O)O[C@]2(C)CC[C@@H]1C[C@@H]1O[C@@]1(C)CC/C=C(\C)CC[C@H]2OC(C)=O
InChIKey:
OEGFAXMPAOHOCK-RAVJQKOMSA-N
InChI:
InChI=1S/C22H32O5/c1-14-7-6-11-21(4)19(26-21)13-17-10-12-22(5,27-20(24)15(17)2)18(9-8-14)25-16(3)23/h7,17-19H,2,6,8-13H2,1,3-5H3/b14-7+/t17-,18-,19+,21+,22-/m1/s1
Calculated Properties
ALogP:
4.254 lipophilicity
TPSA:
65.13 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
5
Rotatable Bonds:
1
Ring Count:
3 (0 aromatic)
Chiral Centers:
5
Fsp³:
0.7273 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007656
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Cembrane diterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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
Antiviral — HepAD38 cells (20 μM screening) — Structured numeric value is not available in this record; see the primary reference. 10.1002/cbdv.202401146 Chemistry & Biodiversity
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Structure enlarged