(Q15410905)

Cynaropicrin (English)

[(3aS,4R,6aS,8R,9aS,9bS)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

5 October 2016

stereoisomer of

1 reference

based on heuristic

inferred from InChI

chemical formula

C₁₉H₂₂O₆

1 reference

Cynaropicrin (English)

18 November 2016

canonical SMILES

C=C1CC(C2C(C3C1CC(C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

1 reference

Cynaropicrin (English)

18 November 2016

isomeric SMILES

C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Cynaropicrin (English)

18 November 2016

2 references

Sesquiterpene lactones. XXXVI. Sesquiterpene lactones in several subgenera of the genus Centaurea L.

Centaurea pterocaula

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Leuzea rhaponticoides

2 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Sesquiterpene lactones. XXXIV. Guaianolides in the genus Leuzea DC.

Psephellus declinatus

2 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Sesquiterpene lactones. XXXIII. Guaianolides in the subgenus Psephellus (Cass.) Schmalh., genus Centaurea L.

Psephellus carthalinicus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus colchicus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Centaurea dealbata

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus daghestanicus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus karabaghensis

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus nogmovii

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus somcheticus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus zangezuri

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Centaurea macrocephala

4 references

Sesquiterpenic lactones from Grossheimia macrocephala. Structure of grosheiminol

Sesquiterpenic lactones from Grossheimia macrocephala. Structure of grosheiminol

ChemInform Abstract: New Cytotoxic Guaianolides and Derivatives from Grosheimia macrocephala.

Sesquiterpenic lactones from Grossheimia macrocephala. Structure of grosheiminol

Volutaria tubuliflora

1 reference

A guaianolide from Amberboa tubuliflora

Anacyclus monanthos

1 reference

New N-alkylamides from Anacyclus pyrethrum

Brachylaena huillensis

3 references

Guaianolides fromBrachylaena species

Guaianolides fromBrachylaena species

Guaianolides from Taeckholmia species

Cheirolophus teydis

2 references

Two derivatives of costic acid from Centaurea arguta

Distribution of sesquiterpene lactones in Cheirolophus from the Canary Islands

Cheirolophus canariensis

3 references

Guaianolides from Centaurea canariensis

Guaianolides from Centaurea canariensis

Guaianolides from Centaurea canariensis

Centaurea hermannii

2 references

Sesquiterpene lactones from Centaurea hermannii

Sesquiterpene lactones from Centaurea hermannii

Centaurea ptosimopappoides

1 reference

Triterpenes of Centaurea ptosimopappoides

Centaurea scoparia

2 references

Constituents of the Egyptian Centaurea scoparia; Part II. Guaianolides of the Aerial Parts

Constituents of the Egyptian Centaurea scoparia; Part II. Guaianolides of the Aerial Parts

Centaurea solstitialis

6 references

Toxic effects of solstitialin a 13-acetate and cynaropicrin from Centaurea solstitialis L. (asteraceae) in cell cultures of foetal rat brain

Guaianolides and lignans from Centaurea solstitialis subs Schouwii

Sesquiterpene lactones from Centaurea solstitialis

Bisabolone derivatives and sesquiterpene lactones from centaurea species

Guaianolides and lignans from Centaurea solstitialis subs Schouwii

Sesquiterpene lactones from Centaurea solstitialis

Centaurothamnus maximus

1 reference

Cytotoxic sesquiterpene lactones from Centaurothamnus maximus and Vicoa pentanema.

Cheirolophus junonianus

1 reference

Distribution of sesquiterpene lactones in Cheirolophus from the Canary Islands

Cheirolophus mauritanicus

1 reference

Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species

Cheirolophus sempervirens

1 reference

Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species

Cheirolophus uliginosus

1 reference

Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species

Cousinia adenosticta

1 reference

Two farnesol derivatives from Cousinia adenostica

Cousinia piptocephala

2 references

Bisabolene derivatives and sesquiterpene lactones from Cousinia species

Bisabolene derivatives and sesquiterpene lactones from Cousinia species

Cynara humilis

1 reference

Sesquiterpene lactones from Cynara humilis

Cynara scolymus

1 reference

Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action

Pseudostifftia kingii

1 reference

Trypanocidal and antimicrobial activities of Moquinia kingii.

Saussurea amurensis

1 reference

Guaianolides of Saussurea amurensis

Saussurea candicans

1 reference

Guaianolides from Saussurea candicans

Saussurea brunneopilosa

1 reference

Studies of Tibetan Medicinal Plants II. Antitumour Activity of Saussurea Eopygmaea

Saussurea eopygmaea

1 reference

Studies of Tibetan Medicinal Plants II. Antitumour Activity of Saussurea Eopygmaea

Saussurea lipschitzii

1 reference

Sesquiterpene lactones in mongolian Saussurea lipshitzii

Saussurea pulchella

2 references

Guaiane sesquiterpene lactones and amino acid-sesquiterpene lactone conjugates from the aerial parts of Saussurea pulchella

Guaiane sesquiterpene lactones and amino acid-sesquiterpene lactone conjugates from the aerial parts of Saussurea pulchella

Saussurea salicifolia

3 references

A sesquiterpene lactone fromSaussurea salicifolia

Further guaianolides from Hymenopappus species

Further guaianolides from saussurea species.

Distephanus glutinosus

1 reference

Chemical constituents from Rehmannia glutinosa

Oligochaeta divaricata

2 references

A guaianolide from Amberboa tubuliflora

Phytochemical Studies on Amberboa ramosa

Artemisia xerophytica

1 reference

Sesquiterpene lactones and other constituents from Artemisia xerophytica

Centaurea behen

1 reference

A guaianolide from Centaurea behen

Centaurea deflexa

1 reference

Anti-proliferative activity of aguerin B and a new rare nor-guaianolide lactone isolated from the aerial parts of Centaurea deflexa

Centaurea kotschyi

1 reference

Guaianolides from Centaurea kotschyi

Pleiotaxis rugosa

1 reference

Sesquiterpene lactones from Oldenburgia arbuscula and Pleiotaxis rugosa

Rhaponticum serratuloides

1 reference

Rhaposerine and rhaserolide, new sesquiterpene lactones fromRhaponticum serratuloides

Saussurea amara

1 reference

Choleretic effects of the Mongolian medicinal plant Saussurea amara in the isolated perfused rat liver.

Himalaiella deltoidea

1 reference

Chemical constituents from Saussurea deltoidea

Tricholepis glaberrima

1 reference

Guaianolides from Tricholepis glaberrima

Volutaria crupinoides

1 reference

Secondary metabolites from Volutaria crupinoides

Lipschitziella deltoidea

1 reference

Chemical constituents from Saussurea deltoidea

Dolomiaea costus

2 references

Cytotoxic and pro-apoptotic activities of cynaropicrin, a sesquiterpene lactone, on the viability of leukocyte cancer cell lines

Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-alpha production in murine macrophage-like cells

Hemisteptia lyrata

1 reference

Guaianolides from Saussurea affinis

Leuzea carthamoides

2 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Sesquiterpene lactones. XXXIV. Guaianolides in the genus Leuzea DC.

Chartolepis glastifolia

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Leuzea rhapontica

2 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Sesquiterpene lactones. XXXIV. Guaianolides in the genus Leuzea DC.

Acroptilon repens

2 references

Bisabolone derivatives and sesquiterpene lactones from centaurea species

Sesquiterpene lactones from Centaurea repens

Achillea fragrantissima

1 reference

Irregular oxygenated monoterpenes from Achillea fragrantissima

Rhaponticum repens

2 references

Bisabolone derivatives and sesquiterpene lactones from centaurea species

Sesquiterpene lactones from Centaurea repens

Psephellus dealbatus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Cynara cardunculus

1 reference

Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action

Psephellus adjaricus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus simplicicaulis

4 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Chromatography of twentysix sesquiterpene lactones fromCentaurea bella

Further sesquiterpene lactones of Centaurea bella

Isolation and chromatography of 15-deoxyrepin and 25 other sesquiterpene lactones from Centaurea bella Trautv

Psephellus bellus

4 references

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Chromatography of twentysix sesquiterpene lactones fromCentaurea bella

Further sesquiterpene lactones of Centaurea bella

Isolation and chromatography of 15-deoxyrepin and 25 other sesquiterpene lactones from Centaurea bella Trautv

Centaurea gabrieljanae

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus hypoleucus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Psephellus leucophyllus

1 reference

A chemotaxonomic study of sesquiterpene lactones from subtribe centaureinae of the compositae

Centaurea melitensis

1 reference

Cynaropicrin: A sesquiterpene lactone from Centaurea americana

1 reference

1 reference

Medical Subject Headings

MeSH descriptor ID

C075687

InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

15 March 2018

Identifiers

InChI

1 reference

Cynaropicrin (English)

18 November 2016

2 references

Cynaropicrin (English)

18 November 2016

ChEBI release 2020-09-01

CAS Registry Number

35730-78-0

2 references

Global Substance Registration System

UNII

M9233789I9

cynaropicrin (English)

18 November 2016

https://commonchemistry.cas.org/detail?cas_rn=35730-78-0

10 April 2021

1 reference

Cynaropicrin (English)

18 November 2016

2 references

Cynaropicrin (English)

18 November 2016

ChEBI ID

4038

mapping relation type

2 references

CYNAROPICRIN (English)

18 November 2016

International Chemical Identifier

InChI

InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

1 reference

CYNAROPICRIN (English)

18 November 2016

1 reference

1 reference

DSSTOX compound identifier

DTXCID501385090

0 references

EC number

689-765-5

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.216.734

27 December 2018

ECHA Substance Infocard ID

cynaropicrin (English)

quotation

CAS no.: 35730-78-0 (English)

100.216.734

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.216.734

27 December 2018

cynaropicrin (English)

quotation

CAS no.: 35730-78-0 (English)

MeSH descriptor ID

C075687

1 reference

Medical Subject Headings

14 March 2018

1 reference

Global Substance Registration System

Cynaropicrin (English)

5 October 2016

2 references

UNII

M9233789I9

cynaropicrin (English)

18 November 2016

0 references

1 reference

Cynaropicrin (English)

inferred by common MeSH mappings on source and on Wikidata

5 October 2016

Freebase ID

/m/0wyntr9

0 references

Microsoft Academic ID

0 references

1 reference

UMLS 2023