4'-Demethylepipodophyllotoxin (CHEM019965)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:39:37 UTC
Update Date2026-04-04 10:17:32 UTC
Accession NumberCHEM019965
Identification
Common Name4'-Demethylepipodophyllotoxin
ClassSmall Molecule
DescriptionAn organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-4'-DemethylepipodophyllotoxinChEBI
4'-Demethyl-9-epipodophyllotoxinChEBI
4'-O-Demethyl-4-epipodophyllotoxinChEBI
4'-O-DemethylepipodophyllotoxinChEBI
DMEPChEBI
Epi-4'-demethylpodophyllotoxinChEBI
4'-Demethyl epipodophyllotoxinMeSH
4'-DemethylepipodophyllotoxinMeSH
Chemical FormulaC21H20O8
Average Molecular Mass400.383 g/mol
Monoisotopic Mass400.116 g/mol
CAS Registry Number6559-91-7
IUPAC Name(10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
Traditional Name(10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
SMILES[H][C@]12COC(=O)[C@]1([H])[C@]([H])(C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@]2([H])O
InChI IdentifierInChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
InChI KeyYVCVYCSAAZQOJI-JHQYFNNDSA-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
  • Methoxyphenol
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Tetralin
  • Benzodioxole
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.84ALOGPS
logP1.48ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity99.42 m³·mol⁻¹ChemAxon
Polarizability39.56 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009500000-417de66041d7ba2d065dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0139100000-94611e3fb44681f14b3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-0249000000-a2f9544be5a24fe06d6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2f7f7444a401e68ba121Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0009000000-e3e5ac446f698d0b93c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fs9-0029000000-69a33af6edc10bea6d20Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID74422
PubChem Compound ID122797
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15246103
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19396467
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21398491
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21706170