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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O2
Molecular Weight 302.451
Optical Activity ( - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOPIMARIC ACID

SMILES

C[C@@]1(CC[C@H]2C(C1)=CC[C@@H]3[C@]2(C)CCC[C@@]3(C)C(O)=O)C=C

InChI

InChIKey=MXYATHGRPJZBNA-KRFUXDQASA-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/h5,7,15-16H,1,6,8-13H2,2-4H3,(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://en.wikipedia.org/wiki/Isopimaric_acid | https://www.ncbi.nlm.nih.gov/pubmed/12237330 | https://www.ncbi.nlm.nih.gov/pubmed/27308214

Isopimaric acid is a widely available tricyclic diterpenoid well represented in the resin of conifers of the genera Pinus, Larix, and Picea. It exhibits interesting biological and pharmaceutical properties such as antimicrobial, antiviral, antiallergenic, and anti‐inflammatory activities. It acts as a large conductance Ca2+activated K+ channel (BK channel) opener. BK channel openers have emerged as potentially useful agents in the therapy of various diseases associated with both the central nervous system and smooth muscle system.

Originator

Hosking, J.R.|Brandt, C.W.
1
Sources: DOI:10.1002/cber.19350680715

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Opener
34
Positive Allosteric Modulator
186
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Atrial fibrillation
131
Sources: DOI: 10.1016/j.bpj.2015.11.2422
 Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Calcium-activated and voltage-gated potassium channels of the pancreatic islet impart distinct and complementary roles during secretagogue induced electrical responses.
2010-09-15
Laser microdissection of conifer stem tissues: isolation and analysis of high quality RNA, terpene synthase enzyme activity and terpenoid metabolites from resin ducts and cambial zone tissue of white spruce (Picea glauca).
2010-06-12
Phytotoxic activity of Salvia x jamensis.
2009-12
A large-conductance (BK) potassium channel subtype affects both growth and mineralization of human osteoblasts.
2009-12
1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca-hydro-phenanthrene-1-carboxylic acid.
2009-05-29
Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test.
2008-11
The use of primary hepatocytes from brown trout (Salmo trutta lacustris) and the fish cell lines RTH-149 and ZF-L for in vitro screening of (anti)estrogenic activity of wood extractives.
2008-04
Isolation of antibacterial diterpenoids from Cryptomeria japonica bark.
2008
Synergistic antinociception by the cannabinoid receptor agonist anandamide and the PPAR-alpha receptor agonist GW7647.
2007-07-02
Stimulation of Ca2+-gated Cl- currents by the calcium-dependent K+ channel modulators NS1619 [1,3-dihydro-1-[2-hydroxy-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2H-benzimidazol-2-one] and isopimaric acid.
2007-06
Pseudomonas reinekei sp. nov., Pseudomonas moorei sp. nov. and Pseudomonas mohnii sp. nov., novel species capable of degrading chlorosalicylates or isopimaric acid.
2007-05
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.
2005-12-03
Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus.
2005-06
[Studies on chemical constituents in bark of Larix olgensis var. koreana].
2005-02
Allelochemical potential of Callicarpa acuminata.
2003-12
Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos.
2003-10-28
Tepidimonas aquatica sp. nov., a new slightly thermophilic beta-proteobacterium isolated from a hot water tank.
2003-09
Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity.
2003-03
Selected resin acids in effluent and receiving waters derived from a bleached and unbleached kraft pulp and paper mill.
2003-01
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.
2002-10
New beyerane and isopimarane diterpenoids from Rhizophora mucronata.
2002-03
Reactivity of Trametes laccases with fatty and resin acids.
2001-04
Patents

Patents

JP2005307045A
3
JP2006083077A
1
JP2010260939A
1

Sample Use Guides

In Vivo Use Guide
1-100 μg/paw
Route of Administration: Other
In Vitro Use Guide
Isopimaric acid was assayed against multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA). The minimum inhibitory concentrations (MIC) were 32-64 ug/mL.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:05:35 GMT 2025
Edited
by admin
on Mon Mar 31 22:05:35 GMT 2025
Record UNII
1E37K85HHK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOPIMARIC ACID
MI  
Common Name English
.DELTA.7,15-ISOPIMARIC ACID
Preferred Name English
PODOCARP-7-EN-15-OIC ACID, 13.BETA.-METHYL-13-VINYL-
Common Name English
7,15-ISOPIMARADIEN-18-OIC ACID
Common Name English
ISOPIMARIC ACID [MI]
Common Name English
ISOPIMARIC ACID A
Common Name English
PODOCARP-7-EN-15-OIC ACID, 13.BETA.-METHYL-13-VINYL-, (-)-
Common Name English
1-PHENANTHRENECARBOXYLIC ACID, 7-ETHENYL-1,2,3,4,4A,4B,5,6,7,8,10,10A-DODECAHYDRO-1,4A,7-TRIMETHYL-, (1R,4AR,4BS,7S,10AR)-
Systematic Name English
Code System Code Type Description
MERCK INDEX
m6516
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY Merck Index
PUBCHEM
442048
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
CAS
5835-26-7
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022233
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
WIKIPEDIA
Isopimaric acid
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
CHEBI
6039
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
FDA UNII
1E37K85HHK
Created by admin on Mon Mar 31 22:05:35 GMT 2025 , Edited by admin on Mon Mar 31 22:05:35 GMT 2025
PRIMARY
NIH
NCATS
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