SCS-C007301
17,18-epoxyloba-16-acetoxy-8,10,13(15)-trien
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Lobane diterpenoids
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Sinularia polydactyla
(NA)
Original source name: Sinularia polydactyla (S. polydactyla)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Sinulariidae
Genus
Sinularia
Species
Sinularia polydactyla
South China Sea
DOI:
10.1016/s1875-5364(20)60025-5
· Chinese Journal of Natural Medicines
Drug-likeness (Lipinski Ro5)
Molecular Weight
346.5 Da
Threshold ≤ 500
ALogP
5.23
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C22H34O3
Molecular Weight:
346.5110 Da
SMILES:
C=C[C@@]1(C)CC[C@H](/C(C)=C/[C@H](OC(C)=O)C2OC2(C)C)C[C@@H]1C(=C)C
InChIKey:
MNPPZSKBNLPHLY-LUMMWHIWSA-N
InChI:
InChI=1S/C22H34O3/c1-9-22(8)11-10-17(13-18(22)14(2)3)15(4)12-19(24-16(5)23)20-21(6,7)25-20/h9,12,17-20H,1-2,10-11,13H2,3-8H3/b15-12+/t17-,18+,19-,20?,22-/m0/s1
Calculated Properties
ALogP:
5.226 lipophilicity
TPSA:
38.83 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
3
Rotatable Bonds:
6
Ring Count:
2
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.6818 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007301
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Lobane 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 |
|---|---|---|---|---|
| Immunomodulatory / Anti-allergic | IC50 | T/B lymphocytes | > 20.0 μmol·L-1 | 10.1016/s1875-5364(20)60025-5 Chinese Journal of Natural Medicines |
| Enzyme inhibition | IC50 | PTP1B enzyme | > 20.0 μmol·L-1 | 10.1016/s1875-5364(20)60025-5 Chinese Journal of Natural Medicines |
| Antibacterial | MIC | Gram-positive and Gram-negative bacteria | > 20.0 μg/mL | 10.1016/s1875-5364(20)60025-5 Chinese Journal of Natural Medicines |