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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 of SHIONONE

SMILES

C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]3[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

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Antioxidant activity of compounds from the medicinal herb Aster tataricus.
2003-10
[Determination of shionone in Radix Asteris by HPLC].
2003-08

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Lipopolysaccharide(LPS)-activated macrophage cells(RAW264.7) were employed as an inflammatory model, which was intervened by the shionone. Western blot was used to detect the protein expression of p-ERK1/2, IκBαand iNOS on the macrophage cells. Compared with the LPS group, the shionone significantly decreased the protein expression of p-ERK1/2 and iNOS and significantly increased the protein expression of IκBα.
Unknown
Name Type Language
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.))-
Preferred Name English
SHIONONE
MI  
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
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
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY
FDA UNII
BT0AMD31UB
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY
PUBCHEM
12315507
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY
MERCK INDEX
m9890
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID80908575
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY
CAS
10376-48-4
Created by admin on Mon Mar 31 20:34:51 GMT 2025 , Edited by admin on Mon Mar 31 20:34:51 GMT 2025
PRIMARY
SUBSTANCE RECORD
Structure of SHIONONE
NIH
NCATS
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