Structure Database (LMSD)

Common Name
(+)-artemisinic acid
Systematic Name
2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
Synonyms
  • artemisinic acid
LM ID
LMPR0103190015
Formula
C15H22O2
Exact Mass
Calculate m/z
234.16198
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

Artemisinic acid is a sesquiterpene that has been isolated from A. annua.1 It has been used in the synthesis of the antimalarial agent artemisinin .2 Artemisinic acid (50-400 µM) decreases triglyceride levels and glycerol-3-phosphate dehydrogenase (GPDH) activity in human adipose tissue-derived mesenchymal stem cells (hAMSCs) in a dose-dependent manner and inhibits adipocyte differentiation when used at a concentration of 200 µM.3 It reduces mRNA expression and protein levels of C/EBPα, C/EBPδ, and PPARγ as well as the ratio of phosphorylated JNK to JNK in hAMSCs. Artemisinic acid also decreases C/EBPα and HMG-CoA reductase mRNA expression and inhibits cholesterol synthesis and melanogenesis in human epidermal melanocytes.4

This information has been provided by Cayman Chemical

References

1. Lee, J., Lee, J., Jung, E., et al. Artemisinic acid inhibits melanogenesis through downregulation of C/EBP α-dependent expression of HMG-CoA reductase gene. Food Chem. Toxicol. 51, 225-230 (2013).
2. Lee, J., Kim, M.-H., Lee, J.-H., et al. Artemisinic acid is a regulator of adipocyte differentiation and C/EBP δ expression. J. Cell. Biochem. 113(7), 2488-2499 (2012).
3. Turconi, J., Griolet, F., Guevel, R., et al. Semisynthetic artemisinin, the chemical path to industrial production. Org. Process Res. Dev. 18(3), 417-422 (2014).
4. Misra, L.N., Ahmad, A., and Thakur, R.S. Crystal structure of artemisinic acid: A possible biogenetic precursor of antimalarial artemisinin from Artemisia annua. J. Nat. Prod. 56(2), 215-219 (1993).

String Representations

InChiKey (Click to copy)
PLQMEXSCSAIXGB-SAXRGWBVSA-N
InChi (Click to copy)
InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1
SMILES (Click to copy)
[C@@]12([H])[C@@]([H])([C@H](C(C(O)=O)=C)CC[C@H]1C)C=C(C)CC2

Other Databases

CHEBI ID
63749
PubChem CID
10922465
Cayman ID
25059

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 2
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 253.00
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 3.65
Molar Refractivity 68.63

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Updated at
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