LIPID MAPS

Structure Database (LMSD)

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Common Name

Epothilone B

Systematic Name

Synonyms

LM ID

LMPK04000041

Formula

C₂₇H₄₁NO₆S

Exact Mass

Calculate m/z

507.26546

Status

Curated

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Classification

Biological Context

Epothilone B (Epo B) is a macrolide that causes the formation of bundles of intracellular microtubules in non-mitotic cells, induces the formation of hyperstable tubulin polymers, and arrests cell cycling in mitosis.^1,2 It induces mitotic arrest at the G2-M transition in Hs578T and HeLa cells (IC50 = 3 and 32 nM, respectively) as well as in multidrug resistant KB3-1 and KBV-1 cells (IC50 = 16 and 92 nM, respectively).¹ Epo B causes cell cycle arrest at nanomolar IC50 values in cell lines from ovarian, breast, lung, colon, prostate, and squamous cancer.³

This information has been provided by Cayman Chemical

References

1. Bollag, D.M., McQueney, P.A., Zhu, J., et al. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 55(11), 2325-2333 (1995).

2. Kowalski, R.J., Giannakakou, P., and Hamel, E. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol(R)). The Journal of Biological Chemisty 272(4), 2534-2541 (1997).

3. Goodin, S., Kane, M.P., and Rubin, E.H. Epothilones: Mechanism of action and biologic activity. J. Clin. Oncol. 22(10), 2015-2025 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Sorangium cellulosum (#56)

Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action.,
Cancer Res, 1995

Pubmed ID: 7757983

Sorangium cellulosum (#56)

Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole sidechain and macrocyclic ring closure,
Tetrahedron Letts, 1997

DOI: 10.1016/S0040-4039(97)00285-2

String Representations

InChiKey (Click to copy)

QXRSDHAAWVKZLJ-PVYNADRNSA-N

InChi (Click to copy)

InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

SMILES (Click to copy)

C1(N=C(SC=1)C)/C=C(/[C@H]1OC(=O)C[C@@H](C(C([C@@H]([C@H]([C@@H](C)CCC[C@@]2(C)O[C@@]2([H])C1)O)C)=O)(C)C)O)\C