herbimycin A   Click here for help

GtoPdb Ligand ID: 5984

Compound class: Natural product
Comment: Herbimycin A is a Streptomyces-derived cell-permeable inhibitor of non-receptor tyrosine kinases [2,4,6].
As with other natural products, there is ambiguity in the precise stereochemisrty presented across web resources eg PubChem CID 6436247 shows an alternate structure.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 152.48
Molecular weight 574.29
XLogP 0.84
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1C(C)C=C(C)C(OC(=O)N)C(OC)C=CC=C(C(=O)NC2=CC(=O)C=C(C(C(CC1OC)C)OC)C2=O)C
Isomeric SMILES COC1[C@@H](C)/C=C(\C)/[C@H](OC(=O)N)C(OC)/C=C\C=C(\C(=O)NC2=CC(=O)C=C([C@@H]([C@H](C[C@@H]1OC)C)OC)C2=O)/C
InChI InChI=1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23?,24-,26+,27?,28-/m0/s1
InChI Key MCAHMSDENAOJFZ-NDSMKMDISA-N

Large-scale screening data

EMD Millipore KinaseProfilerTM screen/Reaction Biology Kinase HotspotSM screen Click here for help
A screen profiling 158 kinase inhibitors (Calbiochem Protein Kinase Inhibitor Library I and II, catalogue numbers 539744 and 539745) for their inhibitory activity at 1µM and 10µM against 234 human recombinant kinases using the EMD Millipore KinaseProfilerTM service.

A screen profiling the inhibitory activity of 178 commercially available kinase inhibitors at 0.5µM against a panel of 300 recombinant protein kinases using the Reaction Biology Corporation Kinase HotspotSM platform.

http://www.millipore.com/techpublications/tech1/pf3036
http://www.reactionbiology.com/webapps/main/pages/kinase.aspx


Reference: 1,3

Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action % Activity remaining at 0.5µM % Activity remaining at 1µM % Activity remaining at 10µM
mitogen-activated protein kinase kinase kinase 14 nd/NIK(MAP3K14) Hs Inhibitor Inhibition 67.9
interleukin 1 receptor associated kinase 1 IRAK1/IRAK1 Hs Inhibitor Inhibition 71.8 106.0 94.0
ribosomal protein S6 kinase A1 Rsk1/RSK1 Hs Inhibitor Inhibition 76.8 115.0 84.0
cyclin dependent kinase 1 CDK1-cyclin B/CDK1-cyclin B Hs Inhibitor Inhibition 77.5 111.0 110.0
serine/threonine kinase 24 MST3/MST3(STK24) Hs Inhibitor Inhibition 79.6 68.0 72.0
serine/threonine-protein kinase MST4 nd/MSTR4 Hs Inhibitor Inhibition 85.3
casein kinase 1 epsilon nd/CK1epsilon Hs Inhibitor Inhibition 85.9
serine/threonine kinase 39 nd/STK39(STLK3) Hs Inhibitor Inhibition 86.5
protein kinase C zeta PKCζ/PKCzeta Hs Inhibitor Inhibition 86.8 104.0 106.0
CDC like kinase 4 nd/CLK4 Hs Inhibitor Inhibition 86.9
Displaying the top 10 targets  View all targets in screen »