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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015310
Secondary Accession Numbers
  • HMDB15310
Metabolite Identification
Common NamePodofilox
DescriptionPodofilox, also known as condylox or podophyllotoxin 7, 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). Podofilox is a drug which is used for treatment of external genital warts (condyloma acuminatum). Podofilox is an extremely weak basic (essentially neutral) compound (based on its pKa). Podofilox is a potentially toxic compound.
Structure
Data?1582753282
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 Weight414.4053
Monoisotopic Molecular Weight414.13146768
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
CAS Registry Number477-47-4
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 Identifier
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 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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.37131661259
DarkChem[M-H]-196.32331661259
DeepCCS[M-2H]-222.07430932474
DeepCCS[M+Na]+197.03130932474
AllCCS[M+H]+195.632859911
AllCCS[M+H-H2O]+193.032859911
AllCCS[M+NH4]+198.032859911
AllCCS[M+Na]+198.732859911
AllCCS[M-H]-199.432859911
AllCCS[M+Na-2H]-199.432859911
AllCCS[M+HCOO]-199.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Podofilox[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]2O5213.4Standard polar33892256
Podofilox[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]2O3328.3Standard non polar33892256
Podofilox[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]2O3492.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Podofilox,1TMS,isomer #1COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1OC3327.9Semi standard non polar33892256
Podofilox,1TBDMS,isomer #1COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1OC3566.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Podofilox GC-EI-TOF (Non-derivatized)splash10-014i-0932100000-95e1178f6bbdd050862b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Podofilox GC-EI-TOF (Non-derivatized)splash10-014i-0932100000-95e1178f6bbdd050862b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Podofilox GC-MS (Non-derivatized) - 70eV, Positivesplash10-0040-1109000000-946a81564d6a1db986132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Podofilox GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-1003900000-d43e5f990afbda30580d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Podofilox GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox LC-ESI-qTOF , Positive-QTOFsplash10-000j-0963000000-4476c6936a37aa211aa32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox LC-ESI-qTof , Positive-QTOFsplash10-0002-0597000000-db51a944dfa407960e8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox LC-ESI-qTof , Positive-QTOFsplash10-00ks-2963000000-b25b106b59de4143117b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-0002-0597000000-db51a944dfa407960e8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-000j-0963000000-4476c6936a37aa211aa32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-00ks-2963000000-b25b106b59de4143117b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-0002-0985000000-53e98e579f100740f3372017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-01q9-0294000000-a3c5accc0b01026c88042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox , positive-QTOFsplash10-0002-0986000000-0ae140ecf023e899576f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 6V, Positive-QTOFsplash10-000i-0964000000-594e28c58db6c7a237022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 6V, Positive-QTOFsplash10-0002-0689100000-26e5d1f1c51b5bc8cd1b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 40V, Positive-QTOFsplash10-015j-0941000000-a2536e1570c993ceaf4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 30V, Positive-QTOFsplash10-000j-0963000000-41a101d931c005b8f2a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 50V, Positive-QTOFsplash10-014r-0940000000-ab1bd1f1613825ab15f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 20V, Positive-QTOFsplash10-0002-0696000000-ebcc3b8fa151aa4628d82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 10V, Positive-QTOFsplash10-0002-0269000000-6681bfe5b9880ae1ea452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 50V, Positive-QTOFsplash10-014r-0940000000-95cc0fdbff989196786a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 30V, Positive-QTOFsplash10-000i-0943000000-f9628ba88402476de0462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Podofilox 10V, Positive-QTOFsplash10-0002-0689100000-e79bf062b65177d2e4092021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 10V, Positive-QTOFsplash10-00kb-0009500000-4616d49ee91153709c322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 20V, Positive-QTOFsplash10-014j-0029100000-07a109dcecbceb6115342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 40V, Positive-QTOFsplash10-0gc0-0029000000-866502321774872dbd1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 10V, Negative-QTOFsplash10-03di-0003900000-0a5bb4d2c68362569d3c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 20V, Negative-QTOFsplash10-02ta-0009200000-dc7b8f1ae65bdd58832d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Podofilox 40V, Negative-QTOFsplash10-014j-1039000000-d11a736e9337d8575e1e2016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01179 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01179 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01179
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00000610
Chemspider ID10162
KEGG Compound IDC10874
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPodophyllotoxin
METLIN IDNot Available
PubChem Compound10607
PDB IDNot Available
ChEBI ID50305
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in structural molecule activity
Specific function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:
TUBB
Uniprot ID:
P07437
Molecular weight:
49670.5
References
  1. Wolff J, Knipling L, Cahnmann HJ, Palumbo G: Direct photoaffinity labeling of tubulin with colchicine. Proc Natl Acad Sci U S A. 1991 Apr 1;88(7):2820-4. [PubMed:2011590 ]
General function:
Involved in structural molecule activity
Specific function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:
TUBA4A
Uniprot ID:
P68366
Molecular weight:
49924.0
References
  1. Labruere R, Gautier B, Testud M, Seguin J, Lenoir C, Desbene-Finck S, Helissey P, Garbay C, Chabot GG, Vidal M, Giorgi-Renault S: Design, synthesis, and biological evaluation of the first podophyllotoxin analogues as potential vascular-disrupting agents. ChemMedChem. 2010 Dec 3;5(12):2016-25. doi: 10.1002/cmdc.201000305. [PubMed:20979080 ]
  2. Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887 ]
  3. Kim ND, Park ES, Kim YH, Moon SK, Lee SS, Ahn SK, Yu DY, No KT, Kim KH: Structure-based virtual screening of novel tubulin inhibitors and their characterization as anti-mitotic agents. Bioorg Med Chem. 2010 Oct 1;18(19):7092-100. doi: 10.1016/j.bmc.2010.07.072. Epub 2010 Aug 6. [PubMed:20810285 ]
  4. Screpanti E, Santaguida S, Nguyen T, Silvestri R, Gussio R, Musacchio A, Hamel E, De Wulf P: A screen for kinetochore-microtubule interaction inhibitors identifies novel antitubulin compounds. PLoS One. 2010 Jul 15;5(7):e11603. doi: 10.1371/journal.pone.0011603. [PubMed:20657644 ]
  5. Alam MA, Naik PK: Applying linear interaction energy method for binding affinity calculations of podophyllotoxin analogues with tubulin using continuum solvent model and prediction of cytotoxic activity. J Mol Graph Model. 2009 Jun-Jul;27(8):930-43. doi: 10.1016/j.jmgm.2009.02.003. Epub 2009 Feb 20. [PubMed:19286405 ]
  6. Clark PI: Clinical pharmacology and schedule dependency of the podophyllotoxin derivatives. Semin Oncol. 1992 Apr;19(2 Suppl 6):20-7. [PubMed:1411635 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Iida A, Kano M, Kubota Y, Koga K, Tomioka K: Podophyllotoxin aza-analogue, a novel DNA topoisomerase II inhibitor. Chem Pharm Bull (Tokyo). 2000 Apr;48(4):486-9. [PubMed:10783066 ]
  2. Zhang YL, Shen YC, Wang ZQ, Chen HX, Guo X, Cheng YC, Lee KH: Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II. J Nat Prod. 1992 Aug;55(8):1100-11. [PubMed:1331331 ]
  3. Terada T, Fujimoto K, Nomura M, Yamashita J, Kobunai T, Takeda S, Wierzba K, Yamada Y, Yamaguchi H: Antitumor agents. I. DNA topoisomerase II inhibitory activity and the structural relationship of podophyllotoxin derivatives as antitumor agents. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2720-7. [PubMed:1334447 ]
  4. Kamal A, Gayatri NL, Reddy DR, Mohan Reddy PS, Arifuddin M, Dastidar SG, Kondapi AK, Rajkumar M: Synthesis and biological evaluation of new 4beta-anilino- and 4beta-imido-substituted podophyllotoxin congeners. Bioorg Med Chem. 2005 Nov 15;13(22):6218-25. Epub 2005 Aug 2. [PubMed:16061385 ]
  5. Ruckdeschel JC: Etoposide in the management of non-small cell lung cancer. Cancer. 1991 Jan 1;67(1 Suppl):250-3. [PubMed:1845848 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]