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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
Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers.
2003 Nov 17
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.
2005 Sep-Oct
Human monocytes kill M-CSF-expressing glioma cells by BK channel activation.
2007 Feb
Immunotherapy of brain cancers: the past, the present, and future directions.
2010
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