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  3. (1S,3S,6R,7S,8S,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-2,4,10-trioxabicyclo[4.3.1]decane-7,8,9-triol

SCS-C003959

(1S,3S,6R,7S,8S,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-2,4,10-trioxabicyclo[4.3.1]decane-7,8,9-triol

Pathway: Terpenoids Superclass: Diterpenoids Class: Serrulatane and Biflorane diterpenoids
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Chemical Structure

Structure of (1S,3S,6R,7S,8S,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-2,4,10-trioxabicyclo[4.3.1]decane-7,8,9-triol
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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.
Download: SDF SMILES

Source Information

Lemnalia bournei (NA)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Nephtheidae Genus Lemnalia Species Lemnalia bournei
Xisha Islands
DOI: 10.1039/np9961300075
Lemnalia bournei (NA)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Nephtheidae Genus Lemnalia Species Lemnalia bournei
South China Sea  · 7 m
DOI: 10.3390/md22040157  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
450.6 Da
Threshold ≤ 500
ALogP
3.55
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C26H42O6
Molecular Weight:
450.6160 Da
SMILES:
CC1=C[C@H]2[C@H]([C@H](C)CCC[C@@H](C)[C@H]3OC[C@H]4O[C@@H](O3)[C@H](O)[C@@H](O)[C@@H]4O)CC=C(C)[C@H]2CC1
InChIKey:
UYNYEKFEWCFAHP-IHMAZEAKSA-N
InChI:
InChI=1S/C26H42O6/c1-14-8-10-18-16(3)9-11-19(20(18)12-14)15(2)6-5-7-17(4)25-30-13-21-22(27)23(28)24(29)26(31-21)32-25/h9,12,15,17-29H,5-8,10-11,13H2,1-4H3/t15-,17-,18-,19+,20-,21-,22-,23+,24-,25+,26+/m1/s1
Calculated Properties
ALogP:
3.548 lipophilicity
TPSA:
88.38 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
11
Fsp³:
0.8462 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003959
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Serrulatane and Biflorane diterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD7060

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
Antibacterial MIC Staphylococcus aureus <= 64.0 μg/mL 10.3390/md22040157 Marine Drugs
Antibacterial MIC Bacillus subtilis <= 64.0 μg/mL 10.3390/md22040157 Marine Drugs
Antitumor — HepG2 cancer cell lines these compounds did not exhibit noticeable cytotoxicities on A549, Hela, and HepG2 cancer cell lines, at 20 μM 10.3390/md22040157 Marine Drugs
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Structure enlarged