Structure Database (LMSD)
Common Name
Epothilone A
Systematic Name
Synonyms
3D model of Epothilone A
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Epothilone A (Epo A) is a biologically active macrolide produced from the fermentation of the soil bacteria S. cellulosum that was discovered as a potent antimicrotubule agent.1,2,3 In competition assays, epo A binds to β-tubulin with a similar order of magnitude as the binding of paclitaxel to β-tubulin (IC50s = 2.3 and 3.6 µM, respectively).1,2,3,4 Epo A is cytotoxic to human T-24 bladder carcinoma cells (IC50 = 0.05 µM in vitro) but has poor pharmacological properties and is 2-fold less potent in stabilizing microtubules compared to epothilone B .1
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).
String Representations
InChiKey (Click to copy)
HESCAJZNRMSMJG-KKQRBIROSA-N
InChi (Click to copy)
InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/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([H])O[C@@]2([H])C1)O)C)=O)(C)C)O)\C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
3
Aromatic Rings
1
Rotatable Bonds
2
Van der Waals Molecular Volume
479.43
Topological Polar Surface Area
111.32
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
7
logP
5.52
Molar Refractivity
133.82
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Updated at
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