CAS 186692-73-9 Epothilone C (HCID 9891226)

概要

Epothilone C is an epothilone that is 1-oxacyclohexadec-13-ene-2,6-dione which is substituted by hydroxy groups at positions 4 and 9, methyl groups at positions 5, 5, 7, and 9, and by a (1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group at position 16 (the 4S,7R,8S,9S,13Z,16S stereoisomer).

名称と識別子

優先名称: Epothilone C
IUPAC: (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
英語名: Epothilone C
分子式: C26H39NO5S
分子量: 477.66

名称と別名

Epothilone C186692-73-9Desoxyepothilone A(-)-Deoxyepothilone AEpo C(-)-Desoxyepothilone A18T00XLN7ECHEBI:80029(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9-tetramethyl-16-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)oxacyclohexadec-13-ene-2,6-dioneOxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4S,7R,8S,9S,13Z,16S)-(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-((E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-1-oxacyclohexadec-13-ene-2,6-dione

名称をさらに表示

Epothilone C USP/EP/BPOxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,4,8-dihydroxy-5,5,7,9-tetramethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dioneOxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5, 7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dioneOxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)- USP/EP/BP

epothilone A, desoxyRefChem:137331Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-((E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4S,7R,8S,9S,13Z,16S)-Epothilone C [WHO-DD]Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-tSCHEMBL4870UNII-18T00XLN7EOxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-

データベース識別子

CAS: 186692-73-9
PubChem CID: 9891226
ChEMBL: CHEMBL319648
ChEBI: CHEBI:80029
UNII: 18T00XLN7E

物性

構造計算による物性

XLogP: 5.1
極性表面積: 125 Å²
水素結合供与体数: 2
水素結合受容体数: 7
回転可能結合数: 2
重原子数: 33
形式電荷: 0
複雑度: 734

物理化学的性質

沸点: 657.7 · 657.7±55.0 °C(Predicted)
比重(密度): 1.097 · 1.097
酸解離定数(Pka): 13.47 · 13.47±0.70(Predicted)
InChIKey: BEFZAMRWPCMWFJ-QJKGZULSSA-N
SMILES: O1[C@H](/C(/C)=C/C2=CSC(C)=N2)CC=CCCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC1=O |c:13|

安全と法規制

危険有害性情報

Regulatory Information · 1 件

Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

化学と産業

応用分野 · 2 件

説明Epothilone C: a tubulin inhibitorEpothilones are 16-membered bacterial macrolides isolated from the bacterium Sorangium cellulosum by Hfle et al., who reported that epothilone A and B had antifungal and cytotoxic activity in 1993. After that, it was reported that epothilones could promote the microtubule polymerization with characteristics and a dynamic mechanism similar to paclitaxel and be bound to tubulin on the paclitaxel microtubule binding site. Other epothilone analogues, such as epothilone C, D, E, and F, have been discovered. Epothilone C is a cytotoxic antitumour natural product. It is produced by the combined action of one nonribosomal peptide synthetase (NRPS) and nine polyketide synthase (PKS) modules in a multienzyme system[1-2].

使用Epothilone C is a related compound of Epothilones, which are a novel class of antineoplastic agents with antitubulin activity. In addition, Epothilones utilize a similar mechanism of action to that of taxanes and are less susceptible to multidrug resistance caused by P-glycoprotein. Studies showed that Epothilones exhibit antitumor activity against human cancer cells that are taxane-resistant.