Compound Selection

Formula: C15H20O3

MW: 248.32

CAS: 20554-84-1

TNP NUMBER: TNP00292

MDL NUMBER: MFCD06668140

IUPAC: (1S,11S)-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0<2,4>]tetradec-7- en-13-one

Smiles: O1C2[C@H]3OC(=O)C([C@@H]3CCC(=CCCC12C)C)=C

isolation from chrisanthemum parthenium

REFERENCE: Kwok, B.H., et al., The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits I?B kinase. Chem. Biol. 8, 759-766, (2001) Pozarowski, P., et al., NF-?B inhibitor sesquiterpene parthenolide induces concurrently atypical apoptosis and cell necrosis: difficulties in identification of dead cells in such cultures. Cytometry 54A, 118-124, (2003) Garcia-Pineres, A.J., et al., Cysteine 38 in p65/NF-?B plays a crucial role in DNA binding inhibition by sesquiterpene lactones. J. Biol. Chem. 276, 39713-39720, (2001) Wen, J., et al., Oxidative stress-mediated apoptosis. The anticancer effect of the sesquiterpene lactone parthenolide. J. Biol. Chem. 277, 38954-38964, (2002) Merck Merck 13,7120 Beilstein Beil. 19,IV,1731 reference RegBook 1 (1), 809:E / Structure Index 1, 126:A:8

SOURCE: isolation from chrisanthemum parthenium

ACCEPTORS: 3

DONORS: 0

ROTATION BONDS: 0

N+O: 3

Chiral Centers: 4

LogP: 4.54

LogS: -4.5

LIPINSKI: 4

Monograph Number: 0007120

Title: Parthenolide

CAS Registry Number: 20554-84-1

CAS Name: (1aR,4E,7aS,10aS,10bS)-2,3,6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one

Additional Names: 4,5a-epoxy-6b-hydroxy-germacra-1(10),11(13)-dien-12-oic acid g-lactone

Molecular Formula: C15H20O3

Molecular Weight: 248.32.

Percent Composition: C 72.55%, H 8.12%, O 19.33%

Literature References: Sesquiterpene lactone found in feverfew, q.v., and in other plants. Isolation from Chrysanthemum parthenium (L.) Bernh. Compositae and characterization: V. Herout et al., Chem. Ind. (London) 1959, 1069; M. Soucek et al., Collect. Czech. Chem. Commun. 26, 803 (1961); from Magnolia grandiflora L., Magnoliaceae: F. S. El-Feraly, Y.-M. Chan, J. Pharm. Sci. 67, 347 (1978). Revised structure and spectral analysis: T. R. Govindachari et al., Tetrahedron 21, 1509 (1965). Absolute configuration: A. S. Bawdekar et al., Tetrahedron Lett. 1966, 1225. Crystal structure: A. Quick, D. Rogers, J. Chem. Soc. Perkin Trans. 2 4, 465 (1976). HPLC determn: D. Strack et al., Z. Naturforsch. 35, 915 (1980). Cytotoxicity: K.-H. Lee et al., Cancer Res. 31, 1649 (1971); L. A. J. O'Neill et al., Br. J. Clin. Pharmacol. 23, 81 (1987).

Properties: Colorless plates, mp 115-116. [a]D20 -81.4 (c = 1.04 in chloroform); [a]D22 -71.4 (c = 0.220 in CH2Cl2). uv max: 214 nm (log e 4.22).

Melting point: mp 115-116

Optical Rotation: [a]D20 -81.4 (c = 1.04 in chloroform); [a]D22 -71.4 (c = 0.220 in CH2Cl2)

Absorption maximum: uv max: 214 nm (log e 4.22)

Chemical Compounds - BioActive Compounds

Structure Search Shop Online Download Databases Request a CD
Structure Search eChemStore Download Request CD

Site Search

Compound Search

share

FacebookTwitterLinkedin

Contact Us

Toll Free 800-574-7391
Phone: 302-292-8500
Fax: 302-292-8520

Chem-TCM is the digital database of molecules from plants used in the traditional Chinese medicine
MyriaScreen II – diversity screening library from Sigma-Aldrich and TimTec
ApexScreen is a collection of 5,040 compounds that were selected to represent the diversity of TimTec stock
Chemistry reagents, HPLC columns, natural compounds
innovative software packages for chemical database management, chemical web server, structure drawing, diversity analysis, clustering, HTS and combinatorial chemistry, prediction of LogP/solubility/Pk, and Spectra Management