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  3. (1R,3R,5S,8E,12E,15S)-5-(hydroxymethyl)-9,13-dimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.03,5]octadeca-8,12-dien-17-one

SCS-C006802

(1R,3R,5S,8E,12E,15S)-5-(hydroxymethyl)-9,13-dimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.03,5]octadeca-8,12-dien-17-one

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

Structure of (1R,3R,5S,8E,12E,15S)-5-(hydroxymethyl)-9,13-dimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.03,5]octadeca-8,12-dien-17-one
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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

Lobophytum crassum (soft coral)
Original source name: L. crassum
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Lobophytum Species Lobophytum crassum
South China Sea
DOI: 10.1038/s41401-024-01347-z  · Acta Pharmacologica Sinica

Drug-likeness (Lipinski Ro5)

Molecular Weight
332.4 Da
Threshold ≤ 500
ALogP
3.46
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C20H28O4
Molecular Weight:
332.4400 Da
SMILES:
C=C1C(=O)O[C@H]2C/C(C)=C/CC/C(C)=C/CC[C@@]3(CO)O[C@@H]3C[C@H]12
InChIKey:
PRUIDJLINDRLON-LDRBAHJUSA-N
InChI:
InChI=1S/C20H28O4/c1-13-6-4-7-14(2)10-17-16(15(3)19(22)23-17)11-18-20(12-21,24-18)9-5-8-13/h7-8,16-18,21H,3-6,9-12H2,1-2H3/b13-8+,14-7+/t16-,17+,18-,20+/m1/s1
Calculated Properties
ALogP:
3.461 lipophilicity
TPSA:
59.06 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
1
Ring Count:
3 (0 aromatic)
Chiral Centers:
4
Fsp³:
0.6500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006802
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
Antitumor IC50 MDA-MB231; A549 — Structured numeric value is not available in this record; see the primary reference. 10.1038/s41401-024-01347-z Acta Pharmacologica Sinica
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Structure enlarged