Structure Database (LMSD)
Common Name
epothilone D
Systematic Name
Synonyms
3D model of epothilone D
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Epothilones are microtubule-stabilizing agents with potential anti-neoplastic actions.1,2,3 They are natural macrolides that have high potency in both taxane-sensitive and taxane-resistant models.2,3 Epothilone D is a desoxy form of epothilone B that inhibits the growth of a variety of cancer cells both in vitro (IC50 values range from 0.97 to 21 nM) and in mice.3,4 Epothilone D is brain penetrant and reduces neurodegeneration in aged tau transgenic mice.5,6 Effects include improved axonal transport, decreased tau neuropathology, and reduced hippocampal neuron loss.5,6 Epothilone D also rescues microtubule defects and attenuates nigrostriatal degeneration in a mouse model of Parkinson’s disease.4
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).
4. Brunden, K.R., Zhang, B., Carroll, J., et al. Epothilone D improves microtubule density, axonal integrity, and cognition in a transgenic mouse model of tauopathy. J. Neurosci. 30(41), 13861-13866 (2010).
References
String Representations
InChiKey (Click to copy)
XOZIUKBZLSUILX-GIQCAXHBSA-N
InChi (Click to copy)
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
SMILES (Click to copy)
C1(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C2N=C(C)SC=2)CC=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
2
Aromatic Rings
1
Rotatable Bonds
2
Van der Waals Molecular Volume
497.66
Topological Polar Surface Area
98.79
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
6
logP
6.13
Molar Refractivity
137.89
Admin
Created at
-
Updated at
19th Sep 2023