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Epothilone A

AlkaPlorer ID: AK004407

Synonym: None

IUPAC Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Structure

SMILES: C/C(=C\C1=CSC(C)=N1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1

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InChI: 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

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InChIKey: HESCAJZNRMSMJG-KKQRBIROSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Sorangium cellulosum Sorangium Polyangiaceae Polyangiales None Myxococcota None Bacteria

Properties Information

Molecule Weight: 493.6660000000003

TPSA？: 109.25

MolLogP？: 4.087420000000003

Number of H-Donors: 2

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens 1A9 IC50 2.2 nM 10.1021/jm050524f
Homo sapiens 1A9/ptx-10 IC50 20.0 nM 10.1021/jm050524f
Homo sapiens 1A9/ptx-22 IC50 5.9 nM 10.1021/jm050524f
Homo sapiens 786-0 GI50 0.1 nM None
Homo sapiens A498 GI50 0.1 nM None
Homo sapiens A549 GI50 0.1 nM None
Homo sapiens A549 IC50 2.2 nM 10.1016/j.bmcl.2009.04.112
Homo sapiens A549 IC50 2.6 nM 10.1016/j.bmc.2009.09.032
Homo sapiens A549 IC50 5000.0 nM 10.1016/j.ejmech.2014.07.035
Homo sapiens ACHN GI50 0.1 nM None
Homo sapiens BT-549 GI50 0.1 nM None
Homo sapiens CAKI-1 GI50 0.1 nM None
Homo sapiens CCRF-CEM GI50 0.1 nM None
Homo sapiens COLO 205 GI50 0.1 nM None
Homo sapiens DU-145 GI50 0.1 nM None
Homo sapiens EKVX GI50 0.1 nM None
Homo sapiens HCC 2998 GI50 0.1 nM None
Homo sapiens HCT-116 GI50 0.1 nM None
Homo sapiens HCT-116 IC50 2.8 nM 10.1021/jm7013452
Homo sapiens HCT-15 GI50 0.1 nM None
Homo sapiens HL-60 GI50 0.1 nM None
Homo sapiens HOP-62 GI50 0.1 nM None
Homo sapiens HOP-92 GI50 3.899 nM None
Homo sapiens Hs-578T GI50 0.1 nM None
Homo sapiens HT-1080 IC50 1.3 nM 10.1016/j.bmc.2009.09.032
Homo sapiens HT-29 GI50 0.1 nM None
Homo sapiens IGROV-1 GI50 0.1 nM None
Homo sapiens K562 GI50 0.1 nM None
Homo sapiens KB IC50 1.91 nM 10.1016/s0960-894x(00)00555-2
Homo sapiens KB 3-1 IC50 2.15 nM 10.1016/s0960-894x(00)00555-2
Homo sapiens KM12 GI50 0.1 nM None
Homo sapiens LOX IMVI GI50 0.1 nM None
Homo sapiens M14 GI50 0.1 nM None
Homo sapiens MCF7 GI50 0.1 nM None
Homo sapiens MCF7 IC50 0.8 nM 10.1016/j.ejmech.2014.07.035
Homo sapiens MCF7 IC50 0.9 nM 10.1016/j.ejmech.2014.07.035
Homo sapiens MCF7 IC50 2.2 nM 10.1021/np500632c
Homo sapiens MCF7 IC50 2.5 nM 10.1016/j.bmc.2009.09.032
Homo sapiens MCF7 IC50 2.6 nM 10.1016/j.bmcl.2009.04.112
Homo sapiens MCF7 IC50 2.9 nM 10.1021/jm7013452
Homo sapiens MDA-MB-231 GI50 0.1 nM None
Homo sapiens MDA-MB-435 GI50 0.1 nM None
Homo sapiens MDA-N GI50 0.1 nM None
Homo sapiens MOLT-4 GI50 0.1 nM None
Homo sapiens NCI/ADR-RES GI50 0.1132 nM None
Homo sapiens NCI-H226 GI50 0.1 nM None
Homo sapiens NCI-H23 GI50 0.1 nM None
Homo sapiens NCI-H322M GI50 0.1 nM None
Homo sapiens NCI-H460 GI50 0.1 nM None
Homo sapiens NCI-H522 GI50 0.1 nM None
Homo sapiens OVCAR-3 GI50 0.1 nM None
Homo sapiens OVCAR-4 GI50 123.88 nM None
Homo sapiens OVCAR-5 GI50 0.1 nM None
Homo sapiens OVCAR-8 GI50 0.1 nM None
Homo sapiens PC-3 FC 0.291 None 10.1038/nchembio790
Homo sapiens PC-3 GI50 0.1 nM None
Homo sapiens RPMI-8226 GI50 0.1 nM None
Homo sapiens RXF 393 GI50 0.1 nM None
Homo sapiens SF-268 GI50 0.1 nM None
Homo sapiens SF-295 GI50 0.1 nM None
Homo sapiens SF-539 GI50 0.1 nM None
Homo sapiens SK-MEL-2 GI50 0.1 nM None
Homo sapiens SK-MEL-5 GI50 0.1 nM None
Homo sapiens SK-OV-3 GI50 0.1 nM None
Homo sapiens SN12C GI50 0.1 nM None
Homo sapiens SNB-19 GI50 0.1 nM None
Homo sapiens SNB-75 GI50 0.1 nM None
Homo sapiens SR GI50 0.1 nM None
Homo sapiens SW-620 GI50 0.1 nM None
Homo sapiens T47D GI50 0.1 nM None
Homo sapiens TK-10 GI50 16.71 nM None
Homo sapiens Tubulin beta-2 chain TP 76.0 % 10.1021/jm050524f
Homo sapiens U-251 GI50 0.1 nM None
Homo sapiens UACC-257 GI50 0.1 nM None
Homo sapiens UACC-62 GI50 0.1 nM None
Homo sapiens UO-31 GI50 0.1 nM None
Mus musculus L929 IC50 0.004 ug.mL-1 10.1021/np000629f
Mus musculus L929 IC50 3.8 nM 10.1021/acs.jnatprod.6b00194
Mus musculus L929 IC50 7.7 nM 10.1021/np500632c
Sus scrofa Sus scrofa EC50 1120.0 nM 10.1016/s0960-894x(00)00555-2
Sus scrofa Sus scrofa Tubulin polymerization 69.0 % 10.1016/s0960-894x(00)00555-2
Sus scrofa Tubulin Inhibition 92.2 % 10.1016/j.bmc.2009.09.032
Sus scrofa Tubulin Inhibition 99.8 % 10.1016/j.bmc.2009.09.032
None ADMET IC50 0.7 nM 10.1016/j.bmc.2009.09.032
None NON-PROTEIN TARGET IC50 1.3 nM 10.1021/np500632c
None NON-PROTEIN TARGET IC50 2.4 nM 10.1021/np500632c
None NON-PROTEIN TARGET IC50 6.4 nM 10.1021/jm7013452
None NON-PROTEIN TARGET IC50 9.6 nM 10.1021/np500632c
None NON-PROTEIN TARGET IC50 70.0 nM 10.1016/j.bmc.2009.09.032
None NON-PROTEIN TARGET IC50 nan ug.mL-1 10.1016/s0960-894x(98)00546-0
None NON-PROTEIN TARGET MIC 5.0 nM 10.1016/j.bmc.2009.09.032
None Unchecked Activity 46.0 % 10.1038/nchembio853
None Unchecked Activity 49.0 % 10.1038/nchembio853
None Unchecked Activity 83.0 % 10.1016/j.bmcl.2009.04.112
None Unchecked Activity 89.0 % 10.1016/j.bmcl.2009.04.112
None Unchecked Activity 95.0 % 10.1038/nchembio853
None Unchecked Activity 96.0 % 10.1038/nchembio853
None Unchecked Activity nan None 10.1016/j.ejmech.2014.07.035
None Unchecked EC50 4600.0 nM 10.1021/jm7013452
None Unchecked Inhibition nan % 10.1016/j.ejmech.2014.07.035
None Unchecked Kd 28.0 nM 10.1038/nchembio853

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001406 C/C(=C\c1csc(C)n1)[C@@H]1C/C=C\CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1>>C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1 47804