podofilox   Click here for help

GtoPdb Ligand ID: 13598

Synonyms: Condylox® | podophyllotoxin
Approved drug PDB Ligand
podofilox is an approved drug (FDA (pre-1990))
Compound class: Natural product
Comment: Podofilox is a lignan found in the roots of Podophyllum species plants. It is a potent tubulin inhibitor (microtubule-destabilising agent).

podofilox is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 92.68
Molecular weight 414.41
XLogP 0.71
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC1=CC(=CC(=C1OC)OC)[C@@H]2C3=C(C=C4C(=C3)OCO4)[C@@H]([C@H]5COC(=O)[C@@H]52)O
Isomeric SMILES COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)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-XVVDYKMHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes. FDA (1990) pre-1990
IUPAC Name Click here for help
(5R,5aR,8aR,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
Condylox® | podophyllotoxin
Database Links Click here for help
ChEMBL Ligand CHEMBL61
GtoPdb PubChem SID 504705417
PubChem CID 10607
RCSB PDB Ligand POD
Search Google for chemical match using the InChIKey YJGVMLPVUAXIQN-XVVDYKMHSA-N
Search Google for chemicals with the same backbone YJGVMLPVUAXIQN
UniChem Compound Search for chemical match using the InChIKey YJGVMLPVUAXIQN-XVVDYKMHSA-N
UniChem Connectivity Search for chemical match using the InChIKey YJGVMLPVUAXIQN-XVVDYKMHSA-N

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MedChemExpress
Podofilox (links to external site)
Cat. No. HY-15552