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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:22 UTC
Update Date2019-07-23 06:08:47 UTC
HMDB IDHMDB0031452
Secondary Accession Numbers
  • HMDB31452
Metabolite Identification
Common NameLignans
DescriptionLignans is found in arrowroot. Podofilox, also called podophyllotoxin, is a purer and more stable form of podophyllin in which only the biologically active portion of the compound is present. Podofilox is used to remove certain types of warts on the outside skin of the genital areas
Structure
Data?1563862127
Synonyms
ValueSource
PicropodophyllotoxinHMDB
PodophyllotoxinHMDB
Chemical FormulaC22H22O8
Average Molecular Weight414.4053
Monoisotopic Molecular Weight414.13146768
IUPAC Name(10R,11S,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 Nameepipodophyllotoxins
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12
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+/m1/s1
InChI KeyYJGVMLPVUAXIQN-BCVBHCCTSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Tetralin
  • Benzodioxole
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Oxolane
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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
Polarizability41.66 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005j-0109000000-14f78dbe46f8312a8fb5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-1003900000-d43e5f990afbda30580dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009500000-4616d49ee91153709c32JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0029100000-07a109dcecbceb611534JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-0029000000-866502321774872dbd1fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003900000-0a5bb4d2c68362569d3cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ta-0009200000-dc7b8f1ae65bdd58832dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-1039000000-d11a736e9337d8575e1eJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.246 +/- 0.269 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.161 +/- 0.135 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.373 +/- 2.313 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.331 +/- 0.419 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01179
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005955
KNApSAcK IDC00033300
Chemspider ID391314
KEGG Compound IDC10871
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443013
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lima LM, Perazzo FF, Tavares Carvalho JC, Bastos JK: Anti-inflammatory and analgesic activities of the ethanolic extracts from Zanthoxylum riedelianum (Rutaceae) leaves and stem bark. J Pharm Pharmacol. 2007 Aug;59(8):1151-8. [PubMed:17725859 ]
  2. Valimaa AL, Honkalampi-Hamalainen U, Pietarinen S, Willfor S, Holmbom B, von Wright A: Antimicrobial and cytotoxic knotwood extracts and related pure compounds and their effects on food-associated microorganisms. Int J Food Microbiol. 2007 Apr 10;115(2):235-43. Epub 2006 Dec 22. [PubMed:17188387 ]
  3. Ma CJ, Sung SH, Kim YC: New neuroprotective dibenzylbutane lignans isolated from Machilus thunbergii. Nat Prod Res. 2010 Apr;24(6):562-8. doi: 10.1080/14786410902823279. [PubMed:20397106 ]
  4. Kassuya CA, Leite DF, de Melo LV, Rehder VL, Calixto JB: Anti-inflammatory properties of extracts, fractions and lignans isolated from Phyllanthus amarus. Planta Med. 2005 Aug;71(8):721-6. [PubMed:16142635 ]
  5. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .