Cepharanthine (CHEM018666)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:42 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018666
Identification
Common NameCepharanthine
ClassSmall Molecule
DescriptionA bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-CepharanthineChEBI
6',12'-Dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthanChEBI
CepharanthinMeSH
Chemical FormulaC37H38N2O6
Average Molecular Mass606.719 g/mol
Monoisotopic Mass606.273 g/mol
CAS Registry Number481-49-2
IUPAC Name(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2¹⁶,¹⁹.1³,¹⁰.1²¹,²⁵.0⁴,⁸.0³¹,³⁵.0¹⁴,³⁹]nonatriaconta-1(33),3(39),4(8),9,16,18,21,23,25(36),31,34,37-dodecaene
Traditional Namecepharanthine
SMILES[H][C@]12CC3=CC(OC4=CC=C(C[C@]5([H])N(C)CCC6=CC7=C(OCO7)C(OC7=C(OC)C=C(CCN1C)C2=C7)=C56)C=C4)=C(OC)C=C3
InChI IdentifierInChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1
InChI KeyYVPXVXANRNDGTA-WDYNHAJCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Oxyneolignan skeleton
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Acetal
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • 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 Solubility0.0048 g/LALOGPS
logP5.31ALOGPS
logP6.42ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity172.96 m³·mol⁻¹ChemAxon
Polarizability65.79 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000049000-6ec61e9173b7989a269bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0000093000-823085996cc1dcfcdf64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-0000090000-1ebadc331082f12f72f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000019000-b2462767da23bd2644feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000096000-4b225a009cdc62267c89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0569-1000190000-024efae1e4e08a0e3fbfSpectrum
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 IDC00001836
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCepharanthine
Chemspider IDNot Available
ChEBI ID3546
PubChem Compound ID10206
Kegg Compound IDC09391
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=26703475