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

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
Allelochemical potential of Callicarpa acuminata.	2003 Dec	14969362
Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos.	2003 Sep-Oct	14577625
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
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
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.

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