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
LM ID
LMPR0104080010
Formula
Exact Mass
Calculate m/z
302.22458
Status
Curated

Classification

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

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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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