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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Synonyms Click here for help
AXL1717 | podofilox
Database Links Click here for help
CAS Registry No. 477-47-4
ChEMBL Ligand CHEMBL283120
DrugBank Ligand DB01179
GtoPdb PubChem SID 223366202
PubChem CID 72435
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Tocris
Picropodophyllotoxin
Cat. No. 2956