PRECOCENE II

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16O3
Molecular Weight	220.2643
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C2C=CC(C)(C)OC2=C1

InChI

InChIKey=PTIDGSWTMLSGAH-UHFFFAOYSA-N

InChI=1S/C13H16O3/c1-13(2)6-5-9-7-11(14-3)12(15-4)8-10(9)16-13/h5-8H,1-4H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3567921 | https://www.ncbi.nlm.nih.gov/pubmed/2598296 | https://www.ncbi.nlm.nih.gov/pubmed/3567921 | https://www.ncbi.nlm.nih.gov/pubmed/7112615 | https://www.ncbi.nlm.nih.gov/pubmed/21941894 | https://www.ncbi.nlm.nih.gov/pubmed/28894278

Precocene II is a cyclic propenylic plant metabolite and asarone analog. It shows antijuvenile hormone activity in insects and inhibits trichothecene production in fungi. Precocene II showed strong hepatotoxic, nephrotoxic and hepatocarcinogenic activity. Precocene II exhibited inhibitory activity on the P-388 cancer cell line and the HT-29 cancer cell line. It is a bioactive component of Ageratum houstonianum, responsible for circadian CLOCK-mediated up-regulation of AQP3 in human keratinocytes. It can be used as a potential adjunct to enhance the treatment of various skin diseases by providing adequate hydration in the epidermis.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin wound 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28894278	Primary		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21941894	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice.	1987 May 1	3567921
Alteration of precocene II-induced hepatotoxicity by modulation of hepatic glutathione levels.	1989	2598296
Effect of precocene on development of ovarian follicles in flesh fly, Sarcophaga ruficornis F.	2004 Jan	15274485
A new chromene isolated from Ageratum conyzoides.	2011 Sep	21941894
Precocene II, a Trichothecene Production Inhibitor, Binds to Voltage-Dependent Anion Channel and Increases the Superoxide Level in Mitochondria of Fusarium graminearum.	2015	26248339
Chemo-profiling and bioassay of phytoextracts from Ageratum conyzoides for acaricidal properties against Rhipicephalus (Boophilus) microplus (Acari: Ixodidae) infesting cattle and buffaloes in India.	2016 Mar	26723275
Agerarin, identified from Ageratum houstonianum, stimulates circadian CLOCK-mediated aquaporin-3 gene expression in HaCaT keratinocytes.	2017 Sep 11	28894278

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

At the highest dose (20 ug/mL) agerarin signifcantly increased AQP3 mRNA levels by 7.17-fold.

Name

Type

Language

PRECOCENE II

Common Name

English

NSC-318792

Code

English

6,7-DIMETHOXY-2,2-DIMETHYLCHROMENE

Systematic Name

English

6,7-DIMETHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN

Systematic Name

English

Code System Code Type Description

NSC

318792