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

개요

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).

이름 및 식별자

우선 이름: 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
영어명: Epothilone C
분자식: C26H39NO5S
분자량: 477.66

이름 및 동의어

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

이름 더 보기

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)-

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 5.1
극성 표면적: 125 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 7
회전 가능 결합 수: 2
무거운 원자 수: 33
형식 전하: 0
복잡도: 734

물리화학적 성질

끓는 점: 657.7 · 657.7±55.0 °C(Predicted)
밀도: 1.097 · 1.097
산도 계수 (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|

안전 및 규제

유해성 정보

Regulatory Information · 1건

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.

화학 및 산업

응용 분야 · 2건

개요Epothilone 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].

용도Epothilone 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.