Structure Database (LMSD)
Common Name
isopimaric acid
Systematic Name
(13S)-pimara-7,15-dien-18-oic acid
Synonyms
- (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
- 4-Epi-isopimaric acid
- Isopimaric acid
3D model of isopimaric acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Isopimaric acid is a diterpenoid resin acid that has been found in P. nigra and has diverse biological activities.1,2,3,4 It is active against clinical isolates of epidemic methicillin-resistant S. aureus (EMRSA; MICs = 32-64 µg/ml).1 Isopimaric acid is an agonist of retinoid X receptor alpha (RXRα), RXRβ, and RXRγ in a reporter assay using HEK293T cells expressing human receptors (EC50s = 26, 32, and 33 µM, respectively).2 It opens large conductance calcium-activated potassium channels (BKCa1.1/KCa1.1) in HEK293 cells expressing recombinant channels and the activating β1 regulatory subunit when used at a concentration of 10 µM.3 Isopimaric acid potentiates reductions in field excitatory postsynaptic potential (fEPSP) slopes in hippocampal slices and decreases escape latency in the Morris water maze in a 3xTg mouse model of Alzheimer’s disease.4 It has been found as an environmental contaminant in pulp and paper mill effluent.5
This information has been provided by Cayman Chemical
References
3. Imaizumi, Y., Sakamoto, K., Yamada, A., et al. Molecular basis of pimarane compounds as novel activators of large-conductance Ca2+-activated K+ channel α-subunit. Mol. Pharmacol. 62(4), 836-846 (2002).
4. Wang, L., Kang, H., Li, Y., et al. Cognitive recovery by chronic activation of the large-conductance calcium-activated potassium channel in a mouse model of Alzheimer’s disease. Neuropharmacology 92, 8-15 (2015).
String Representations
InChiKey (Click to copy)
MXYATHGRPJZBNA-KRFUXDQASA-N
InChi (Click to copy)
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1
SMILES (Click to copy)
[C@]12(CC=C3C[C@@](C=C)(CC[C@@]3([C@@]1(C)CCC[C@]2(C(O)=O)C)[H])C)[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
3
Aromatic Rings
0
Rotatable Bonds
2
Van der Waals Molecular Volume
327.14
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
5.21
Molar Refractivity
89.54
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Updated at
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