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SCS-C001892

3-dehydroxylpresinularolide B

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids
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Chemical Structure

Structure of 3-dehydroxylpresinularolide B
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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

Lobophytum crassum (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Lobophytum Species Lobophytum crassum
Sanya  · -20 m
DOI: 10.1021/np800081p  · Journal of Natural Products
Lobophytum sp. (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Lobophytum Species NA
South China Sea  · 8 m
DOI: 10.3390/md11041162  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
316.4 Da
Threshold ≤ 500
ALogP
4.25
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C20H28O3
Molecular Weight:
316.4000 Da
SMILES:
C=C1C(=O)O[C@H]2C/C(C)=C/CC/C(C)=C/CC/C(CO)=C/C[C@H]12
InChIKey:
KXVIJXIRUBWYDB-WJEGPQOWSA-N
InChI:
InChI=1S/C20H28O3/c1-14-6-4-8-15(2)12-19-18(16(3)20(22)23-19)11-10-17(13-21)9-5-7-14/h7-8,10,18-19,21H,3-6,9,11-13H2,1-2H3/b14-7+,15-8+,17-10-/t18-,19+/m1/s1
Calculated Properties
ALogP:
4.250 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
1
Ring Count:
2 (0 aromatic)
Chiral Centers:
2
Fsp³:
0.5500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001892
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Cembrane diterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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 inhibition A-549, P-388 95.7% (A-549), 100% (P-388) inhibition at 10^-5 mol/L 10.1021/np800081p Journal of Natural Products
Antibacterial inhibition rate Staphylococcus aureus, S. pneumoniae, Pseudomonas aeruginosa, Saccharomyces cerevisiae, Aspergillus fumigatus — Structured numeric value is not available in this record; see the primary reference. 10.3390/md11041162 Marine Drugs
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Structure enlarged