SCS-C008131
sarcocraol A
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 crassocaule
(NA)
Original source name: Sarcophyton crassocaule | S. crassocaule
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Alcyoniidae
Genus
Sarcophyton
Species
Sarcophyton crassocaule
South China Sea
· 20 m
DOI:
10.3390/md23120450
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
348.4 Da
Threshold ≤ 500
ALogP
3.59
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:
C20H28O5
Molecular Weight:
348.4390 Da
SMILES:
C/C1=C\[C@]23OC[C@]4(C)O[C@]24CC[C@@](C)(/C=C/C[C@@]2(C)O[C@@H]2CC1)OO3
InChIKey:
VDGYAYNUMBBCIF-QKAHVYIISA-N
InChI:
InChI=1S/C20H28O5/c1-14-6-7-15-17(3,22-15)9-5-8-16(2)10-11-19-18(4,23-19)13-21-20(19,12-14)25-24-16/h5,8,12,15H,6-7,9-11,13H2,1-4H3/b8-5+,14-12+/t15-,16-,17-,18+,19+,20-/m1/s1
Calculated Properties
ALogP:
3.585 lipophilicity
TPSA:
52.75 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
5
Rotatable Bonds:
0
Ring Count:
5
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.8000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008131
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 |
|---|---|---|---|---|
| Metabolic / Lipid regulation | transcriptional activity | PPAR-γ | compound 1 at 10 μM exhibited significant and selective agonist activity toward PPAR-γ | 10.3390/md23120450 Marine Drugs |
| Metabolic / Lipid regulation | protein expression | PPAR-γ | 4.65 fold | 10.3390/md23120450 Marine Drugs |
| Metabolic / Lipid regulation | protein expression | PPAR-γ | 6.76 fold | 10.3390/md23120450 Marine Drugs |
| Antitumor | glucose uptake | HepG2 cells (2.5 μM) | 1.18 fold | 10.3390/md23120450 Marine Drugs |
| Antitumor | glucose uptake | HepG2 cells (5 μM) | 1.45 fold | 10.3390/md23120450 Marine Drugs |
| Antitumor | glucose uptake | HepG2 cells (10 μM) | 1.9 fold | 10.3390/md23120450 Marine Drugs |
| Metabolic / Lipid regulation | lipid droplet formation | 3T3-L1 cells (10 μM) | 1.63 fold | 10.3390/md23120450 Marine Drugs |
| Antitumor | cell viability | HepG2 cells (10 μM and 50 μM | > 90.0 % | 10.3390/md23120450 Marine Drugs |