SCS-C000165
[(1S,6R,7S,8R)-7-[(3E)-4,8-dimethylnona-3,7-dienyl]-7-methyl-8-(5-oxo-2H-furan-3-yl)-3-bicyclo[4.2.0]oct-2-enyl]methyl acetate
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Sacculatane diterpenoids
Chemical Structure
![Structure of [(1S,6R,7S,8R)-7-[(3E)-4,8-dimethylnona-3,7-dienyl]-7-methyl-8-(5-oxo-2H-furan-3-yl)-3-bicyclo[4.2.0]oct-2-enyl]methyl acetate](/scsmarinenp/static/images/structures/SCS-C000165.png)
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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
Luffariella variabilis
(NA)
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Dictyoceratida
Family
Thorectidae
Genus
Luffariella
Species
Luffariella variabilis
Yongle Islands
· 16.5665N, 111.6863E
DOI:
10.1021/acs.jnatprod.0c01026
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
426.6 Da
Threshold ≤ 500
ALogP
6.09
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H38O4
Molecular Weight:
426.6000 Da
SMILES:
CC(=O)OCC1=C[C@H]2[C@@H](CC1)[C@](C)(CC/C=C(\C)CCC=C(C)C)[C@@H]2C1=CC(=O)OC1
InChIKey:
MFTDYYWRENBODO-GAQXCQJQSA-N
InChI:
InChI=1S/C27H38O4/c1-18(2)8-6-9-19(3)10-7-13-27(5)24-12-11-21(16-30-20(4)28)14-23(24)26(27)22-15-25(29)31-17-22/h8,10,14-15,23-24,26H,6-7,9,11-13,16-17H2,1-5H3/b19-10+/t23-,24+,26+,27-/m0/s1
Calculated Properties
ALogP:
6.094 lipophilicity
TPSA:
52.60 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
4
Rotatable Bonds:
9
Ring Count:
3
(0 aromatic)
Chiral Centers:
4
Fsp³:
0.6296 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000165
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Sacculatane 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 |
|---|---|---|---|---|
| Antitumor | IC50 | K562 | 7.4 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |
| Antitumor | IC50 | L-02 | 13.0 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |
| Antitumor | IC50 | ASPC-1 | > 30.0 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |
| Antitumor | IC50 | MDA-MB-231 | 11.0 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |
| Antitumor | IC50 | ASPC-1 | > 30.0 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |
| Antitumor | IC50 | K562 | > 30.0 μM | 10.1021/acs.jnatprod.0c01026 Journal of Natural Products |