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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

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

HIDE SMILES / InChI

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

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
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
Immunotherapy of brain cancers: the past, the present, and future directions.
2010
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
Molecular mechanisms of paraptosis induction: implications for a non-genetically modified tumor vaccine.
2009
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

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:36:54 GMT 2025
Edited
by admin
on Mon Mar 31 20:36:54 GMT 2025
Record UNII
88R98Z71NI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-2956
Preferred Name English
PIMARIC ACID
MI  
Common Name 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 Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
CAS
127-27-5
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
MERCK INDEX
m8810
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY Merck Index
PUBCHEM
220338
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
FDA UNII
88R98Z71NI
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
NSC
2956
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
WIKIPEDIA
PIMARIC ACID
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID80858728
Created by admin on Mon Mar 31 20:36:54 GMT 2025 , Edited by admin on Mon Mar 31 20:36:54 GMT 2025
PRIMARY