Podofilox (CHEM003577)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2014-09-05 17:14:40 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003577
Identification
Common NamePodofilox
ClassSmall Molecule
DescriptionA lignan (lignans) found in podophyllin resin from the roots of podophyllum plants. It is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. It is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antimitotic Agent
  • Antineoplastic Agent, Phytogenic
  • Drug
  • Ester
  • Ether
  • Keratolytic Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Tubulin Modulator
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-PodophyllotoxinChEBI
9-HYDROXY-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-D][1,3]dioxol-6(5ah)-oneChEBI
CondyloxChEBI
Podophyllinic acid lactoneChEBI
Podophyllotoxin 7ChEBI
PPTChEBI
PodophyllotoxinKegg
Podophyllinate lactoneGenerator
Ardern brand OF podophyllotoxinHMDB
CondylineHMDB
Hamilton brand OF podophyllotoxinHMDB
Oclassen brand OF podophyllotoxinHMDB
WartecHMDB
CPH86HMDB
EpipodophyllotoxinHMDB
Fides ecopharma brand OF podophyllotoxinHMDB
Paladin brand OF podophyllotoxinHMDB
PODOCON-25HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomerHMDB
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomerHMDB
WarticonHMDB
Newport brand OF podophyllotoxinHMDB
PodofilmHMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomerHMDB
Wolff brand OF podophyllotoxinHMDB
Canderm brand OF podophyllotoxinHMDB
Paddock brand OF podophyllotoxinHMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomerHMDB
Stiefel brand OF podophyllotoxinHMDB
Yamanouchi brand OF podophyllotoxinHMDB
PodofiloxChEBI
Chemical FormulaC22H22O8
Average Molecular Mass414.405 g/mol
Monoisotopic Mass414.131 g/mol
CAS Registry Number477-47-4
IUPAC Name(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
Traditional Namecondylox
SMILES[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O
InChI IdentifierInChI=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 KeyYJGVMLPVUAXIQN-XVVDYKMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassPodophyllotoxins
Direct ParentPodophyllotoxins
Alternative Parents
Substituents
  • Podophyllotoxin
  • 1-aryltetralin lignan
  • Linear furanonaphthodioxole
  • Naphthofuran
  • Tetralin
  • Benzodioxole
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point228°C
Boiling PointNot Available
Solubility100 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.37ALOGPS
logP1.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.02ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area92.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.9 m³·mol⁻¹ChemAxon
Polarizability41.71 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0932100000-95e1178f6bbdd050862bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0932100000-95e1178f6bbdd050862bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0040-1109000000-946a81564d6a1db98613Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-1003900000-d43e5f990afbda30580dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-000j-0963000000-4476c6936a37aa211aa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0597000000-db51a944dfa407960e8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00ks-2963000000-b25b106b59de4143117bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0597000000-db51a944dfa407960e8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0963000000-4476c6936a37aa211aa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00ks-2963000000-b25b106b59de4143117bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0985000000-53e98e579f100740f337Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-0294000000-a3c5accc0b01026c8804Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0986000000-0ae140ecf023e899576fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0964000000-594e28c58db6c7a23702Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0689100000-26e5d1f1c51b5bc8cd1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-015j-0941000000-a2536e1570c993ceaf4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000j-0963000000-41a101d931c005b8f2a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014r-0940000000-ab1bd1f1613825ab15f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0696000000-ebcc3b8fa151aa4628d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0269000000-6681bfe5b9880ae1ea45Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014r-0940000000-95cc0fdbff989196786aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0943000000-f9628ba88402476de046Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0689100000-e79bf062b65177d2e409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009500000-4616d49ee91153709c32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0029100000-07a109dcecbceb611534Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-0029000000-866502321774872dbd1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003900000-0a5bb4d2c68362569d3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ta-0009200000-dc7b8f1ae65bdd58832dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-1039000000-d11a736e9337d8575e1eSpectrum
Toxicity Profile
Route of ExposureTopical application of 0.05 mL of 0.5% podofilox solution to external genitalia did not result in detectable serum levels. Applications of 0.1 to 1.5 mL resulted in peak serum levels of 1 to 17 ng/mL one to two hours after application.
Mechanism of ToxicityEtoposide, a semisynthetic derivative of podofilox, induces DNA breakage through its inhibition of topoisomerase II. The drug is most active in the late S and early G2 phases of the cell cycle. Teniposide is an analog with very similar pharmacologic characteristics. Podofilox derivatives display binding activity to the enzyme topoisomerase II during the late S and early G2 stage. For instance, etoposide binds and stabilizes the temporary break caused by the enzyme, disrupts the reparation of the break through which the double-stranded DNA passes, and consequently stops DNA unwinding and replication. Mutants resistant to either podofilox, or to its topoisomerase II inhibitory derivatives such as etoposide (VP-16), have been described in Chinese hamster cells. The mutually exclusive cross-resistance patterns of these mutants provide a highly specific mean to distinguish the two kinds of podofilox derivatives. Mutant Chinese hamster cells resistant to podofilox are affected in a protein P1 that was later identified as the mammalian HSP60 or chaperonin protein. (Wikipedia)
Metabolism Half Life: 1.0 to 4.5 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor treatment of external genital warts (Condyloma acuminatum).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01179
HMDB IDHMDB0015310
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000610
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPodophyllotoxin
Chemspider ID10162
ChEBI ID50305
PubChem Compound ID10607
Kegg Compound IDC10874
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15803102
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22621772
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23161544
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23798883
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8112825