picropodophyllin   Click here for help

GtoPdb Ligand ID: 7873

Synonyms: AXL1717 | podofilox
Compound class: Synthetic organic
Comment: Picropodophyllin is a lignan extract from podophyllin resin produced in the roots of podophyllum plants. It is an epimer of picropodophyllotoxin. Picropodophyllin has been suggested to act as a selective inhibitor of the insulin-like growth factor 1 receptor (IGF1R) and has potential antineoplastic activity [1-2]. Its effect via IGF1R have been questioned [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 92.68
Molecular weight 414.13
XLogP 1.64
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O
Isomeric SMILES COc1cc(cc(c1OC)OC)[C@H]1[C@@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
InChI InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
InChI Key YJGVMLPVUAXIQN-HAEOHBJNSA-N
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Summary of Clinical Use Click here for help
Picropodophyllin (with research code AXL1717) is being assessed in a Phase 1/II clinical trial (NCT01721577) for recurrent malignant astrocytomas.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
IGF1R is overexpressed in a variety of human cancers, and plays an important role in the growth and survival of many types of cancer cells. Therefore, IGF1R is a target of pharmaceutical intervention in such diseases.