(Q27106570)

Eupatoriopicrin (English)

[(3aS,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

5 October 2016

stereoisomer of

2 references

inferred from InChIKey

[(3aR,4R,6E,10E,11aS)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

1 reference

[(3aR,4R,6Z,10Z,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

1 reference

[(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

1 reference

chemical formula

C₂₀H₂₆O₆

1 reference

Eupatoriopicrin (English)

5 October 2016

canonical SMILES

CC1=CC2C(C(CC(=CCC1)C)OC(=O)C(=CCO)CO)C(=C)C(=O)O2

1 reference

Eupatoriopicrin (English)

5 October 2016

isomeric SMILES

C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/CC1)/C)OC(=O)/C(=C/CO)/CO)C(=C)C(=O)O2

1 reference

Eupatoriopicrin (English)

5 October 2016

found in taxon

Eupatorium cannabinum

10 references

Allergenic sesquiterpene lactones fromEupatorium cannabinum L. andKaunia rufescens (Lund ex de Candolle)?

Choleretic and hepatoprotective properties of Eupatorium cannabinum in the rat.

Enhanced cytostatic activity of the sesquiterpene lactone eupatoriopicrin by glutathione depletion

Eupatoriopicrin 19-O-Linolenoate and Other Constituents from Eupatorium cannabium

Evaluation of thein vitroCytotoxicity of some Sesquiterpene Lactones on a Human Lung Carcinoma Cell Line Using the Fast Green Dye Exclusion Assay

Investigation of the anti-tumor action of eupatoriopicrin against the Lewis lung tumour

On terpenes. CXLV. Constitution of eupatoriopicrin, a germacranolide from Eupatorium cannabinum L.

Reduced levels of glutathione in liver and tumour tissue of the mouse after administration of eupatoriopicrin

Role of membrane lipid composition in the cytotoxicity of the sesquiterpene lactone eupatoriopicrin

Allergic contact dermatitis caused by Artemisia and Chrysanthemum species. The role of sesquiterpene lactones

Stevia sarensis

2 references

The first 12.8β-germacrolide and other constituents from bolivian Stevia species

The first 12.8β-germacrolide and other constituents from bolivian Stevia species

Disynaphia multicrenulata

1 reference

Heliangolides and germacrolides from Disynaphia multicrenulata

Florestina tripteris

1 reference

Eupatolide and borneol derivatives from Florestina tripteris

Kyrsteniopsis dibollii

1 reference

Unusual norhomoditerpenes and other constituents from Kyrsteniopsis dibollii

Pericome caudata

1 reference

Guaianolides from Pericome caudata

Perityle vaseyi

1 reference

Sesquiterpene lactones from Perityle vaseyi

Stevia alpina

1 reference

Sesquiterpene lactones from Stevia alpina var. glutinosa

Brickellia californica

1 reference

Guaianolides and labdanes from Brickellia species

Hymenopappus scabiosaeus

1 reference

Further guaianolides from Hymenopappus species

Perityle emoryi

1 reference

Sesquiterpene lactones from Perityle emoryi

Stevia maimarensis

1 reference

Sesquiterpene lactones and other constituents of Stevia maimarensis and Synedrellopsis grisebachii

Stevia procumbens

1 reference

Sesquiterpene Lactones and Flavones from Stevia procumbens

Carphochaete pringlei

1 reference

A cyclopropanoheliangolide and guaianolides from cronquistia pringlei

Eupatorium glehnii

1 reference

Seven Germacranolides, Eupaglehnins A, B, C, D, E, and F, and 2α-Acetoxyepitulipinolide from Eupatorium glehni.

Identifiers

InChI

InChI=1S/C20H26O6/c1-12-5-4-6-13(2)10-17(26-20(24)15(11-22)7-8-21)18-14(3)19(23)25-16(18)9-12/h6-7,9,16-18,21-22H,3-5,8,10-11H2,1-2H3/b12-9+,13-6+,15-7+/t16-,17-,18+/m1/s1

1 reference

Eupatoriopicrin (English)

VWJYWGYJIDQUEG-DKDOXNMLSA-N

5 October 2016

InChIKey

2 references

Eupatoriopicrin (English)

5 October 2016

ChEBI release 2020-09-01

2 references

Eupatoriopicrin (English)

VWJYWGYJIDQUEG-DKDOXNMLSA-N

5 October 2016

InChIKey

8 April 2021

https://commonchemistry.cas.org/detail?cas_rn=6856-01-5

1 reference

eupatoriopicrin (English)

5 October 2016

2 references

Eupatoriopicrin (English)

matched by identifier from

5 October 2016

InChIKey

VWJYWGYJIDQUEG-DKDOXNMLSA-N

ChEBI ID

4937

mapping relation type

2 references

Eupatoriopicrin (English)

matched by identifier from

5 October 2016

International Chemical Identifier

InChI

InChI=1S/C20H26O6/c1-12-5-4-6-13(2)10-17(26-20(24)15(11-22)7-8-21)18-14(3)19(23)25-16(18)9-12/h6-7,9,16-18,21-22H,3-5,8,10-11H2,1-2H3/b12-9+,13-6+,15-7+/t16-,17-,18+/m1/s1

1 reference

reason for deprecated rank

cannot be confirmed by other sources

1 reference

Eupatoriopicrin (English)

5 October 2016

1 reference