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SCS-C001850

(S)-5-Hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one

Pathway: Polyketides Glycoside
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Chemical Structure

Structure of (S)-5-Hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one
Loading 3D structure...
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

Sinularia tumulosa (soft coral)
Original source name: Sinularia tumulosa (S. tumulosa)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sarcophytidae Genus Sclerophytum Species Sclerophytum tumulosum
South China Sea  · -20 m
DOI: 10.1016/j.bioorg.2020.104167  · Bioorganic Chemistry
Sinularia verruca (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia verruca
Ximao Island  · -8 m
DOI: 10.1021/acs.jnatprod.6b00031  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
198.3 Da
Threshold ≤ 500
ALogP
2.15
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:
C11H18O3
Molecular Weight:
198.2600 Da
SMILES:
CCCCC[C@]1(O)OC(=O)C(C)=C1C
InChIKey:
VJZWZDQDXPADSE-NSHDSACASA-N
InChI:
InChI=1S/C11H18O3/c1-4-5-6-7-11(13)9(3)8(2)10(12)14-11/h13H,4-7H2,1-3H3/t11-/m0/s1
Calculated Properties
ALogP:
2.148 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
1 (0 aromatic)
Chiral Centers:
1
Fsp³:
0.7273 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001850
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
Glycoside:
Yes
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
Anti-inflammatory IC50 LPS-induced TNF-α release 12.0 μM 10.1016/j.bioorg.2020.104167 Bioorganic Chemistry
Antitumor IC50 A549; SNU-398; Capan-1 cell lines the cytotoxic activity of all compounds against A549, HT-29, SNU-398, and Capan-1 cell lines were evaluated, showing that all compounds showed low cytotoxicity. 10.1016/j.bioorg.2020.104167 Bioorganic Chemistry
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Structure enlarged