SCS-C008387
cembranoid 3
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
Sarcophyton ehrenbergi
(soft coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Alcyoniidae
Genus
Sarcophyton
Species
Sarcophyton ehrenbergi
South China Sea
· approximately 10 m
DOI:
10.1021/acs.jnatprod.6c00463
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
320.5 Da
Threshold ≤ 500
ALogP
3.91
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H32O3
Molecular Weight:
320.4730 Da
SMILES:
C=C(C)[C@@H]1/C=C/[C@](C)(O)CC/C=C(\C)CC[C@@H]2O[C@@]2(C)[C@H](O)C1
InChIKey:
XFDBMBGGXWSWEJ-NJSXDRDHSA-N
InChI:
InChI=1S/C20H32O3/c1-14(2)16-10-12-19(4,22)11-6-7-15(3)8-9-18-20(5,23-18)17(21)13-16/h7,10,12,16-18,21-22H,1,6,8-9,11,13H2,2-5H3/b12-10+,15-7+/t16-,17-,18+,19-,20+/m1/s1
Calculated Properties
ALogP:
3.915 lipophilicity
TPSA:
52.99 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
1
Ring Count:
2
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.7000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008387
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 release inhibition | LPS-stimulated RAW264.7 macrophages | compound 3 as the most active compound, showing the greatest reduction of NO release and TNFα secretion among the isolates | 10.1021/acs.jnatprod.6c00463 Journal of Natural Products |
| Anti-inflammatory | TNFα secretion inhibition | TNFα | compound 3 as the most active compound, showing the greatest reduction of NO release and TNFα secretion among the isolates | 10.1021/acs.jnatprod.6c00463 Journal of Natural Products |
| Anti-inflammatory | IκBα degradation inhibition | IκBα | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.6c00463 Journal of Natural Products |
| Antibacterial | growth inhibition | six pathogenic bacterial strains | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.6c00463 Journal of Natural Products |