SCS-C007654

methyl 2-((1R,2S,5S,7S,9R,12R,13S)-2-(acetyloxy)-12-hydroxy-1,5,12-trimethyl-6,16-dioxatricyclo[11.2.1.0^{5,7}]hexadecan-9-yl)prop-2-enoate

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids

Chemical Structure

$Structure of methyl 2-((1R,2S,5S,7S,9R,12R,13S)-2-(acetyloxy)-12-hydroxy-1,5,12-trimethyl-6,16-dioxatricyclo[11.2.1.0^{5,7}]hexadecan-9-yl)prop-2-enoate$

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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.

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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

424.5 Da

Threshold ≤ 500

ALogP

3.07

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H36O7

Molecular Weight:

424.5340 Da

SMILES:

C=C(C(=O)OC)[C@@H]1CC[C@@](C)(O)[C@@H]2CC[C@@](C)(O2)[C@@H](OC(C)=O)CC[C@]2(C)O[C@H]2C1

InChIKey:

                        AVJJAJDAJIWWOI-VSMZHHACSA-N
                        
                    

InChI:

InChI=1S/C23H36O7/c1-14(20(25)27-6)16-7-10-21(3,26)17-8-11-22(4,29-17)18(28-15(2)24)9-12-23(5)19(13-16)30-23/h16-19,26H,1,7-13H2,2-6H3/t16-,17+,18+,19+,21-,22-,23+/m1/s1

Calculated Properties

ALogP:

3.074 lipophilicity

TPSA:

94.59 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.8261 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007654

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Diterpenoids

NPClassifier Class:

Cembrane diterpenoids

Glycoside:

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
Antiviral	structure-activity relationship	SAR analysis	— Structured numeric value is not available in this record; see the primary reference.	10.1002/cbdv.202401146 Chemistry & Biodiversity

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