Structure Database (LMSD)

Common Name
alantolactone
Systematic Name
(3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one
Synonyms
  • Alantolactone
  • Helenin
  • Eupatal
LM ID
LMPR0103190013
Formula
C15H20O2
Exact Mass
Calculate m/z
232.14633
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Eudesmane sesquiterpenoids [PR010319]

Biological Context

Alantolactone is a sesquiterpene lactone that has been found in Inula species and has diverse biological activities.1,2,3 It inhibits LPS-induced increases in nitric oxide, IL-6, and TNF-α production in RAW 246.7 cells by 76.09, 81.54, and 71.23%, respectively, when used at a concentration of 10 μM.1 Alantolactone (40 μM) decreases cell viability, glutathione (GSH) levels, and the mitochondrial membrane potential, induces apoptosis, and increases generation of reactive oxygen species (ROS) in HepG2 cells.2 It inhibits phosphorylation and nuclear translocation of STAT3 in MDA-MB-231 cells in a concentration-dependent manner.3 Alantolactone (2.5 mg/kg) reduces tumor growth in an MDA-MB-231 mouse xenograft model.

This information has been provided by Cayman Chemical

References

1. Kumar, C., Kumar, A., Nalli, Y., et al. Design, synthesis and biological evaluation of alantolactone derivatives as potential anti-inflammatory agents. Med. Chem. Res. 28(1), 849-856 (2019).
2. Khan, M., Li, T., Khan, M.K.A., et al. Alantolactone induces apoptosis in HepG2 cells through GSH depletion, inhibition of STAT3 activation, and mitochondrial dysfunction. Biomed Res. Int. 2013(719858), 1-11 (2012).
3. Chun, J., Li, R.-J., Cheng, M.-S., et al. Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells. Cancer Lett. 357(1), 393-403 (2014).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Inula helenium (#55635)
Magnoliopsida (#3398)
The structure of alantolactone. II. The conversion of alantolactone into dihydroeudesmol.,
Chem Pharm Bull (Tokyo), 1958
Pubmed ID: 13537178

String Representations

InChiKey (Click to copy)
PXOYOCNNSUAQNS-AGNJHWRGSA-N
InChi (Click to copy)
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
SMILES (Click to copy)
O1[C@]2([H])C[C@@]3(C)CCC[C@H](C)C3=C[C@]2([H])C(=C)C1=O

Other Databases

Wikipedia
Helenin
KEGG ID
C09289
CHEBI ID
2540
PubChem CID
72724
Cayman ID
29762

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 3
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 240.64
Topological Polar Surface Area 28.37
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 3.53
Molar Refractivity 66.84

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Created at
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Updated at
20th Feb 2025