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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, also known as podophyllotoxin, 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). Structure 3 is a neolignan, a structure formed by joining the two propylbenzene residues at other than the β-carbon atom of the propyl side chain. Lignans is an extremely weak basic (essentially neutral) compound (based on its pKa). Major compound(s) in bold. Lignans are one of the major classes of phytoestrogens, which are estrogen-like chemicals and also act as antioxidants. Outside of the human body, lignans has been detected, but not quantified in, arrowroots and flaxseeds. This could make lignans a potential biomarker for the consumption of these foods. Secoisolariciresinol and matairesinol were the first plant lignans identified in foods. Mammalian lignan precursors as aglycones (µg/100 g). Some examples of lignans are enterolignans, enterodiol and enterolactone.
Structure
Data?1563862127
Synonyms
ValueSource
PicropodophyllotoxinHMDB
PodophyllotoxinHMDB
LignansMeSH
NeolignansMeSH
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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005j-0109000000-14f78dbe46f8312a8fb5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-1003900000-d43e5f990afbda30580dSpectrum
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
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005955
KNApSAcK IDC00002619 C00033300
Chemspider ID391314
KEGG Compound IDC10871
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLignan
METLIN IDNot Available
PubChem Compound443013
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .