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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-08-28 17:02:36 UTC
Update Date2021-09-26 22:47:35 UTC
HMDB IDHMDB0242210
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Deoxypodophyllotoxin
DescriptionIsoanthricin belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Isoanthricin is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-deoxypodophyllotoxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Deoxypodophyllotoxin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
IsodeoxypodophyllotoxinMeSH
Deoxypodophyllotoxin, (5R-(5alpha,5abeta,8aalpha))-isomerMeSH
Deoxypodophyllotoxin, (5alpha,5aalpha,8aalpha)-(+-)-isomerMeSH
Deoxypodophyllotoxin, (5alpha,5aalpha,8abeta)-(+-)-isomerMeSH
Deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8abeta))-isomerMeSH
DeoxypicropodophyllinMeSH
Deoxypodophyllotoxin, (5R-(5alpha,5abeta,8abeta))-isomerMeSH
DeoxypodophyllotoxinMeSH
Deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8aalpha))-isomerMeSH
Chemical FormulaC22H22O7
Average Molecular Weight398.411
Monoisotopic Molecular Weight398.136553048
IUPAC Name10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
Traditional Name10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)CC2=CC3=C(OCO3)C=C12
InChI Identifier
InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3
InChI KeyZGLXUQQMLLIKAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassNot Available
Direct ParentLignan lactones
Alternative Parents
Substituents
  • Lignan lactone
  • 1-aryltetralin lignan
  • Linear furanonaphthodioxole
  • Naphthofuran
  • Tetralin
  • Benzodioxole
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.23ALOGPS
logP2.81ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.49 m³·mol⁻¹ChemAxon
Polarizability40.96 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
DeepCCS[M-2H]-221.14130932474
DeepCCS[M+Na]+196.42130932474
AllCCS[M+H]+192.332859911
AllCCS[M+H-H2O]+189.832859911
AllCCS[M+NH4]+194.732859911
AllCCS[M+Na]+195.432859911
AllCCS[M-H]-193.532859911
AllCCS[M+Na-2H]-193.132859911
AllCCS[M+HCOO]-192.832859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxypodophyllotoxin GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-0009000000-c1517c76117f4825ef812021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxypodophyllotoxin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxypodophyllotoxin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxypodophyllotoxin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxypodophyllotoxin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 10V, Positive-QTOFsplash10-000t-0049000000-0e05a46f37a5dfe1f0922021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 20V, Positive-QTOFsplash10-000t-0059000000-5d3608d6e0b15d777b022021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 40V, Positive-QTOFsplash10-0fms-0169000000-b1d50fdfb49beba2caa02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 10V, Negative-QTOFsplash10-0002-0109000000-2315e944b5a648d40c512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 20V, Negative-QTOFsplash10-0gba-0009000000-3ede7117463f37b235ee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxypodophyllotoxin 40V, Negative-QTOFsplash10-0mjj-1079000000-69e7ad9bb3211d83576b2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2203
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]