Structure Database (LMSD)

Common Name
Epothilone B
Systematic Name
Synonyms
LM ID
LMPK04000041
Formula
C27H41NO6S
Exact Mass
Calculate m/z
507.265461
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Macrolides and lactone polyketides [PK04]

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).

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

Other Databases

Wikipedia
Epothilone_B
KEGG ID
C12154
CHEBI ID
31550
PubChem CID
448013
Cayman ID
10924
PDB ID
EPB

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 1
Rotatable Bonds 2
Van der Waals Molecular Volume 496.73
Topological Polar Surface Area 111.32
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 5.91
Molar Refractivity 138.43

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Updated at
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