SHIONONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H50O
Molecular Weight	426.7174
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(=O)[C@H](C)[C@@]1(C)CC[C@@]3([H])[C@@]2(C)CC[C@@]4(C)C[C@](C)(CCC=C(C)C)CC[C@]34C

InChI

InChIKey=HXPXUNQUXCHJLL-LZQQOHPBSA-N

InChI=1S/C30H50O/c1-21(2)10-9-14-26(4)16-19-30(8)25-13-15-28(6)22(3)23(31)11-12-24(28)29(25,7)18-17-27(30,5)20-26/h10,22,24-25H,9,11-20H2,1-8H3/t22-,24+,25-,26+,27-,28+,29-,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C30H50O
Molecular Weight	426.7174
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.en.cnki.com.cn/Article_en/CJFDTotal-BXYY201604085.htm | https://www.ncbi.nlm.nih.gov/pubmed/%2025701752

The root of Aster tataricus L. f. (recorded in all versions of Chinese Pharmacopoeia) is a traditional Chinese medicine with the function of dispelling phlegm and relieving cough for more than 2000 years. Shionone is one of the principal components. It was extracted from Aster tataricus and possesses anti-inflammatory effects. The anti-inflammatory mechanism of shionone was related to a decrease in the phosphorylation level of ERK1/2 protein and IκBα and the protein expression of iNOS. In addition, shionone can inhibit the activity of ubiquitin-specific protease 2 (USP2) and provide a lead compound for the future development of new USP2 inhibitors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ubiquitin carboxyl-terminal hydrolase 2 1 Target ID: O75604 Gene ID: 9099.0 Gene Symbol: USP2 Target Organism: Homo sapiens (Human) Sources: https://www.researchgate.net/publication/288731011_Inhibitory_effect_of_shionone_on_activity_of_ubiquitin-specific_protease_2	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
		2025701752
[Determination of shionone in Radix Asteris by HPLC].	2003 Aug	15015355

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:23:33 GMT 2023` Edited by `admin` on `Sat Dec 16 00:23:33 GMT 2023`
Record UNII	BT0AMD31UB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SHIONONE

Common Name

English

D-HOMO-5.ALPHA.-ANDROSTAN-17-ONE, 3.ALPHA.,5,8,17A.BETA.-TETRAMETHYL-3-(4-METHYL-3-PENTENYL)-

Common Name

English

2(1H)-CHRYSENONE, HEXADECAHYDRO-1,4B,6A,8,10A,12A-HEXAMETHYL-8-(4-METHYL-3-PENTENYL)-, (1R-(1.ALPHA.,4A.BETA.,4B.ALPHA.,6A.BETA.,8.BETA.,10A.ALPHA.,10B.BETA.,12A.ALPHA.))-

Common Name

English

SHIONONE [MI]

Common Name

English

2(1H)-CHRYSENONE, HEXADECAHYDRO-1,4B,6A,8,10A,12A-HEXAMETHYL-8-(4-METHYL-3-PENTEN-1-YL)-, (1R,4AS,4BS,6AS,8R,10AR,10BS,12AS)-

Systematic Name

English

D:A-FRIEDO-18,19-SECOLUP-19-EN-3-ONE

Common Name

English

SHIONON

Common Name

English

Code System Code Type Description

CHEBI

63459