U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
Reactivity of Trametes laccases with fatty and resin acids.
2001 Apr
Antimicrobial diterpenes from the stem bark of Mitrephora celebica.
2002 Aug
Pimarane diterpene from Viguiera arenaria (Asteraceae) inhibit rat carotid contraction.
2002 Oct
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.
2002 Oct
Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers.
2003 Nov 17
Evidence for the mechanisms underlying the effects of pimaradienoic acid isolated from the roots of Viguiera arenaria on rat aorta.
2004 Jan
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.
2004 Nov
Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid.
2005 Aug
Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb.
2005 Jan
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.
2005 Sep-Oct
Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus lusitanica Mill. from Cameroon.
2006 Jan 16
Human monocytes kill M-CSF-expressing glioma cells by BK channel activation.
2007 Feb
Pimaradienoic acid inhibits vascular contraction and induces hypotension in normotensive rats.
2008 Apr
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 Dec 28
Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.
2008 Mar
Design, synthesis and characterization of podocarpate derivatives as openers of BK channels.
2008 Oct 1
Molecular mechanisms of paraptosis induction: implications for a non-genetically modified tumor vaccine.
2009
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 Apr 25
Immunotherapy of brain cancers: the past, the present, and future directions.
2010
Bioactive diterpenes from the aerial parts of Anisochilus harmandii.
2010 May
Subgroup 4 R2R3-MYBs in conifer trees: gene family expansion and contribution to the isoprenoid- and flavonoid-oriented responses.
2010 Sep
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 Sat Dec 16 00:30:35 GMT 2023
Edited
by admin
on Sat Dec 16 00:30:35 GMT 2023
Record UNII
88R98Z71NI
Record Status Validated (UNII)
Record Version
  • Download
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