ISOPIMARIC ACID

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 Search

SMILES

[H][C@]12CC[C@@](C)(CC1=CC[C@@]3([H])[C@@](C)(CCC[C@]23C)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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16114093
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcium-activated potassium channel alpha/beta 1 5 Target ID: CHEMBL3038495 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12237330	Opener 34
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21793559	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25577958	Primary	Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17434479	Primary	Preclinical	Unknown Approved Use Unknown
Staphylococcal infections 24 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27769946 https://www.ncbi.nlm.nih.gov/pubmed/16114093	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

Title	Date	PubMed
Reactivity of Trametes laccases with fatty and resin acids.	2001 Apr	11341313
New beyerane and isopimarane diterpenoids from Rhizophora mucronata.	2002 Mar	11991193
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.	2002 Oct	12237330
Allelochemical potential of Callicarpa acuminata.	2003 Dec	14969362
Selected resin acids in effluent and receiving waters derived from a bleached and unbleached kraft pulp and paper mill.	2003 Jan	12503767
Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity.	2003 Mar	12612410
Tepidimonas aquatica sp. nov., a new slightly thermophilic beta-proteobacterium isolated from a hot water tank.	2003 Sep	14529180
Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos.	2003 Sep-Oct	14577625
[Studies on chemical constituents in bark of Larix olgensis var. koreana].	2005 Feb	15724403
Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus.	2005 Jun	16114093
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.	2005 Sep-Oct	16320613
Synergistic antinociception by the cannabinoid receptor agonist anandamide and the PPAR-alpha receptor agonist GW7647.	2007 Jul 2	17434479
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 Jun	17347326
Pseudomonas reinekei sp. nov., Pseudomonas moorei sp. nov. and Pseudomonas mohnii sp. nov., novel species capable of degrading chlorosalicylates or isopimaric acid.	2007 May	17473234
Isolation of antibacterial diterpenoids from Cryptomeria japonica bark.	2008	18780250
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 Apr	18206344
Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test.	2008 Nov	18424098
Phytotoxic activity of Salvia x jamensis.	2009 Dec	20120094
A large-conductance (BK) potassium channel subtype affects both growth and mineralization of human osteoblasts.	2009 Dec	19776394
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 May 29	21583270
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 Jun 12	20540781
Calcium-activated and voltage-gated potassium channels of the pancreatic islet impart distinct and complementary roles during secretagogue induced electrical responses.	2010 Sep 15	20643768

Patents

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 `Sat Dec 16 08:27:04 GMT 2023` Edited by `admin` on `Sat Dec 16 08:27:04 GMT 2023`
Record UNII	1E37K85HHK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPIMARIC ACID

Common 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

.DELTA.7,15-ISOPIMARIC ACID

Common Name

English

Code System Code Type Description

MERCK INDEX

m6516