GRINDELIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H32O3
Molecular Weight	320.4663
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@@]13CC[C@@](C)(CC(O)=O)O3

InChI

InChIKey=XLWWERNKTLITEF-MVJPYGJCSA-N

InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15-,18-,19-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H32O3
Molecular Weight	320.4663
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26119826 | https://www.ncbi.nlm.nih.gov/pubmed/23831507
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24383718

Grindelic acid is a labdane-type diterpene that was reported as the main secondary metabolite from Grindelia chiloensis Cabr and G. pulchella Dunal var. pulchella (Asteraceae). Recent studies demonstrated potential pharmaceutical applications for grindelic acid and its synthetic derivatives. Grindelic acid is a NOX4 inhibitor (IC50 2 uM). Grindelic acid’s mechanism of action is unknown, but it inhibited neither ROS in a cell-free membrane-based NOX4 assay nor from the purified NOX4 dehydrogenase domain. Grindelic acid demonstrates in vitro antitumor activity against human breast, cervix, lung,colon cancer.

Approval Year

Targets

Primary Target	Pharmacology	Potency
NADPH oxidase 4 3 Target ID: CHEMBL1250375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24383718	Inhibitor 8504	2.06 µM [IC50]
SW1573 1 Target ID: CHEMBL612570 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Inhibitor 8504
HBL-100 1 Target ID: CHEMBL614811 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Inhibitor 8504
WiDr 1 Target ID: CHEMBL614647 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Primary	Basic research	Unknown Approved Use Unknown
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831507	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Exploring diterpene metabolism in non-model species: transcriptome-enabled discovery and functional characterization of labda-7,13E-dienyl diphosphate synthase from Grindelia robusta.	2015-09	26119826
Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives.	2013-09	23831507

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Grindelic acid inhibited NOX4 with IC50 2 uM in cell-free assay.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 11:38:22 GMT 2025` Edited by `admin` on `Wed Apr 02 11:38:22 GMT 2025`
Record UNII	4QX9FCD1IN
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

(-)-GRINDELIC ACID

Preferred Name

English

GRINDELIC ACID

Common Name

English

GRINDELIC ACID [MI]

Common Name

English

SPIRO(FURAN-2(3H),1'(4'H)-NAPHTHALENE)-5-ACETIC ACID, 4,4'A,5,5',6',7',8',8'A-OCTAHYDRO-2',5,5',5',8'A-PENTAMETHYL-, (1'R,4'AS,5S,8'AS)-

Systematic Name

English

SPIRO(FURAN-2(3H),1'(4'H)-NAPHTHALENE)-5-ACETIC ACID, 4,4'A,5,5',6',7',8',8'A-OCTAHYDRO-2',5,5',5',8'A-PENTAMETHYL-, (1'R-(1'.ALPHA.(S*),4'A.ALPHA.,8'A.BETA.))-

Systematic Name

English

LABD-7-EN-15-OIC ACID, 9,13-EPOXY-

Systematic Name

English

Code System Code Type Description

FDA UNII

4QX9FCD1IN