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  3. methyl 2-((1S,3R,6R,7S,10E,14S)-7-(acetyloxy)-6-hydroxy-6,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadec-10-en-3-yl)prop-2-enoate

SCS-C007662

methyl 2-((1S,3R,6R,7S,10E,14S)-7-(acetyloxy)-6-hydroxy-6,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadec-10-en-3-yl)prop-2-enoate

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

Structure of methyl 2-((1S,3R,6R,7S,10E,14S)-7-(acetyloxy)-6-hydroxy-6,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadec-10-en-3-yl)prop-2-enoate
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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
408.5 Da
Threshold ≤ 500
ALogP
3.86
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C23H36O6
Molecular Weight:
408.5350 Da
SMILES:
C=C(C(=O)OC)[C@@H]1CC[C@@](C)(O)[C@@H](OC(C)=O)CC/C(C)=C/CC[C@]2(C)O[C@H]2C1
InChIKey:
WIUZTEVKBSGUCK-UBBYPUMYSA-N
InChI:
InChI=1S/C23H36O6/c1-15-8-7-12-23(5)20(29-23)14-18(16(2)21(25)27-6)11-13-22(4,26)19(10-9-15)28-17(3)24/h8,18-20,26H,2,7,9-14H2,1,3-6H3/b15-8+/t18-,19+,20+,22-,23+/m1/s1
Calculated Properties
ALogP:
3.863 lipophilicity
TPSA:
85.36 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
6
Rotatable Bonds:
3
Ring Count:
2 (0 aromatic)
Chiral Centers:
5
Fsp³:
0.7391 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007662
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 HBV DNA inhibition HepAD38 cells (20 μM, 3 days) All the isolated compounds were evaluated for anti-HBV and cytotoxic effects at 20 μM in HepAD38 cells 10.1002/cbdv.202401146 Chemistry & Biodiversity
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Structure enlarged