ingenol mebutate   Click here for help

GtoPdb Ligand ID: 7443

Synonyms: PEP-005 | Picato®
Approved drug PDB Ligand
ingenol mebutate is an approved drug (FDA & EMA (2012))
Comment: Ingenol mebutate is extracted from the plant Euphorbia peplus.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 104.06
Molecular weight 430.24
XLogP 3.21
No. Lipinski's rules broken 0
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Canonical SMILES CC=C(C(=O)OC1C(=CC23C1(O)C(O)C(=CC(C3=O)C1C(CC2C)C1(C)C)CO)C)C
Isomeric SMILES C/C=C(\C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C)/C
InChI InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
Bioactivity Comments
Although a binding study across PKC isoforms shows no selectivity in binding, PKC δ is believed to be the primary target of ingenol mebutate based on other differential actions of the drug on this particular isozyme [2]. For example, Figure 9 in [2] indicates that the kinase activity of PKCδ is activated more potently by ingenol mebutate than is PKCα.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
protein kinase C beta Hs Activator Activation 10.0 pKi - 2
pKi 10.0 (Ki 1.05x10-10 M) [2]
protein kinase C gamma Hs Activator Activation 9.8 pKi - 2
pKi 9.8 (Ki 1.62x10-10 M) [2]
protein kinase C epsilon Hs Activator Activation 9.8 pKi - 2
pKi 9.8 (Ki 1.71x10-10 M) [2]
protein kinase C alpha Hs Activator Activation 9.5 pKi - 2
pKi 9.5 (Ki 3x10-10 M) [2]
protein kinase C delta Primary target of this compound Hs Activator Activation 9.4 pKi - 2
pKi 9.4 (Ki 3.76x10-10 M) [2]