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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
Structure of PIMARIC ACID

SMILES

[H][C@]12CC[C@@](C)(C=C)C=C1CC[C@@]3([H])[C@@](C)(CCC[C@]23C)C(O)=O

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

HIDE SMILES / InChI

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Evidence for the mechanisms underlying the effects of pimaradienoic acid isolated from the roots of Viguiera arenaria on rat aorta.
2004 Jan
Design, synthesis and characterization of podocarpate derivatives as openers of BK channels.
2008 Oct 1
Bioactive diterpenes from the aerial parts of Anisochilus harmandii.
2010 May
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
Name Type Language
PIMARIC ACID
MI  
Common Name English
NSC-2956
Code English
DEXTROPIMARIC ACID
Common Name English
PIMARIC ACID [MI]
Common Name English
(1R,4AR,4BS,7S,10AR)-7-ETHENYL-1,2,3,4,4A,4B,5,6,7,9,10,10A-DODECAHYDRO-1,4A,7-TRIMETHYL-1-PHENANTHRENECARBOXYLIC ACID
Common Name English
.ALPHA.-PIMARIC ACID
Common Name English
D-PIMARIC ACID
Common Name English
Code System Code Type Description
MESH
C008911
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
CAS
127-27-5
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
MERCK INDEX
m8810
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY Merck Index
PUBCHEM
220338
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
FDA UNII
88R98Z71NI
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
NSC
2956
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
WIKIPEDIA
PIMARIC ACID
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID80858728
Created by admin on Sat Dec 16 00:30:35 GMT 2023 , Edited by admin on Sat Dec 16 00:30:35 GMT 2023
PRIMARY