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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22O2
Molecular Weight 234.334
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOPETASOL

SMILES

C[C@H]1[C@H](O)CCC2=CC(=O)C(C[C@]12C)=C(C)C

InChI

InChIKey=TVDMUSYVWJLIDK-PSOPSSQASA-N
InChI=1S/C15H22O2/c1-9(2)12-8-15(4)10(3)13(16)6-5-11(15)7-14(12)17/h7,10,13,16H,5-6,8H2,1-4H3/t10-,13+,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H22O2
Molecular Weight 234.334
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Sources: doi:10.1016/0031-9422(83)80099-5
Curator's Comment: description was created based on several sources, including: doi:10.1016/S0040-4020(01)96317-3 http://www.acgpubs.org/RNP/2014/Volume8/Issue%201/21-RNP-1211-204.pdf

The components of several Petasites species have been investigated and shown to include petasin furanopetasin derivatives belonging to the eremophilane type of sesquiterpene, and bakkenolide derivatives. It has been reported that the petasin derivatives have spasmolytic properties and bakkenolide-A has cytotoxic activity. Natural is (+)-isopetasol. It was also isolated from the rhizomes of Ligularia fischeri grown in Henan province of China. Isopetasol derivatives with an unsaturated acid ester moiety will selectively inhibit RNA synthesis in the ascites tumor of mouse.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Phytotoxic eremophilane sesquiterpenes from the coprophilous fungus Penicillium sp. G1-a14.
2015 Feb 27
Patents

Patents

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 11:11:04 GMT 2023
Edited
by admin
on Sat Dec 16 11:11:04 GMT 2023
Record UNII
3612JYH60G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOPETASOL
Common Name English
EREMOPHILA-7(11),9-DIEN-8-ONE, 3.ALPHA.-HYDROXY-
Common Name English
(+)-ISOPETASOL
Common Name English
2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-6-HYDROXY-4A,5-DIMETHYL-3-(1-METHYLETHYLIDENE)-, (4AR,5R,6R)-
Systematic Name English
2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-6-HYDROXY-4A,5-DIMETHYL-3-(1-METHYLETHYLIDENE)-, (4AR-(4A.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
Code System Code Type Description
CAS
469-67-0
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY
PUBCHEM
11746594
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY
FDA UNII
3612JYH60G
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Petasin chemovar-Eremophilane