Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H30O2 |
| Molecular Weight | 302.451 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]1(CC[C@H]2C(CC[C@@H]3[C@]2(C)CCC[C@@]3(C)C(O)=O)=C1)C=C
InChI
InChIKey=MHVJRKBZMUDEEV-APQLOABGSA-N
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/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1
| Molecular Formula | C20H30O2 |
| Molecular Weight | 302.451 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12237330Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22705379
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12237330
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22705379
Pimaric acid is a carboxylic acid from the resin acid group. It is a BK-channel opener and inhibits TNF-alpha induced signaling by downregulating NF-kB and AP-1.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2800 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12237330 |
|||
Target ID: map04668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22705379 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Subgroup 4 R2R3-MYBs in conifer trees: gene family expansion and contribution to the isoprenoid- and flavonoid-oriented responses. | 2010-09 |
|
| Bioactive diterpenes from the aerial parts of Anisochilus harmandii. | 2010-05 |
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| Immunotherapy of brain cancers: the past, the present, and future directions. | 2010 |
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| 1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodeca-hydro-phenanthrene-1-carboxylic acid. | 2009-04-25 |
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| Molecular mechanisms of paraptosis induction: implications for a non-genetically modified tumor vaccine. | 2009 |
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| Ent-pimara-8(14), 15-dien-19-oic acid isolated from the roots of Aralia cordata inhibits induction of inflammatory mediators by blocking NF-kappaB activation and mitogen-activated protein kinase pathways. | 2008-12-28 |
|
| Design, synthesis and characterization of podocarpate derivatives as openers of BK channels. | 2008-10-01 |
|
| Pimaradienoic acid inhibits vascular contraction and induces hypotension in normotensive rats. | 2008-04 |
|
| Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production. | 2008-03 |
|
| Human monocytes kill M-CSF-expressing glioma cells by BK channel activation. | 2007-02 |
|
| Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus lusitanica Mill. from Cameroon. | 2006-01-16 |
|
| Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa. | 2005-12-03 |
|
| Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid. | 2005-08 |
|
| Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb. | 2005-01 |
|
| A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds. | 2004-11 |
|
| Evidence for the mechanisms underlying the effects of pimaradienoic acid isolated from the roots of Viguiera arenaria on rat aorta. | 2004-01 |
|
| Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers. | 2003-11-17 |
|
| Pimarane diterpene from Viguiera arenaria (Asteraceae) inhibit rat carotid contraction. | 2002-10 |
|
| Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. | 2002-10 |
|
| Antimicrobial diterpenes from the stem bark of Mitrephora celebica. | 2002-08 |
|
| Reactivity of Trametes laccases with fatty and resin acids. | 2001-04 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12237330
To measure BK activation whole-cell patch clamp on HEK293, expressing BKalpha, was used. The Ca2 concentration in the pipette solution was fixed at pCa 6.5 using a Ca2-EGTA buffer. Depolarization from -60 to -30 mV induced outward currents in both native HEK and HEKBK1. Application of PiMA in a concentration range of 1 to 10 uM increased outward currents in a dose-dependent fashion in HEKBK1 but did not change in native HEK.
| Substance Class |
Chemical
Created
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| Record UNII |
88R98Z71NI
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| Record Status |
Validated (UNII)
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127-27-5
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m8810
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220338
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88R98Z71NI
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2956
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PIMARIC ACID
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DTXSID80858728
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