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  3. 3-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

SCS-C000108

3-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Pathway: Terpenoids Superclass: Diterpenoids Class: Halimane diterpenoids Glycoside
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Chemical Structure

Structure of 3-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
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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

Sarcotragus sp. (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Irciniidae Genus Sarcotragus Species NA
Xisha Islands
DOI: 10.1021/acs.jnatprod.2c00937  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
318.5 Da
Threshold ≤ 500
ALogP
4.37
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:
C20H30O3
Molecular Weight:
318.4570 Da
SMILES:
C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CCC1=CC(=O)OC1O
InChIKey:
XKQKOMBDTAHBFA-MDXWAKLHSA-N
InChI:
InChI=1S/C20H30O3/c1-13-7-8-15-16(6-5-10-19(15,2)3)20(13,4)11-9-14-12-17(21)23-18(14)22/h6,12-13,15,18,22H,5,7-11H2,1-4H3/t13-,15-,18?,20-/m0/s1
Calculated Properties
ALogP:
4.367 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
3
Ring Count:
3 (0 aromatic)
Chiral Centers:
4
Fsp³:
0.7500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000108
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Halimane diterpenoids
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
Antitumor IC50 K562 7.19 μM 10.1021/acs.jnatprod.2c00937 Journal of Natural Products
Antitumor IC50 ASPC-1 17.95 μM 10.1021/acs.jnatprod.2c00937 Journal of Natural Products
Antitumor IC50 H69AR 27.49 μM 10.1021/acs.jnatprod.2c00937 Journal of Natural Products
Antitumor IC50 L-02 24.05 μM 10.1021/acs.jnatprod.2c00937 Journal of Natural Products
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Structure enlarged