(+)-Syringaresinol (CHEM029789)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:25:12 UTC
Update Date2016-11-09 01:18:57 UTC
Accession NumberCHEM029789
Identification
Common Name(+)-Syringaresinol
ClassSmall Molecule
DescriptionThe (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,4'-(1S,3AR,4S,6ar)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)ChEBI
Syringa-resinolMeSH
SyringaresinolMeSH
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomerMeSH
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomerMeSH
(+)-Lirioresinol BPhytoBank
(+)-SyringaresinolPhytoBank
(±)-SyringaresinolPhytoBank
dl-SyringaresinolPhytoBank
Chemical FormulaC22H26O8
Average Molecular Mass418.437 g/mol
Monoisotopic Mass418.163 g/mol
CAS Registry Number21453-69-0
IUPAC Name4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
Traditional Name(+)-syringaresinol
SMILES[H][C@]12CO[C@H](C3=CC(OC)=C(O)C(OC)=C3)[C@@]1([H])CO[C@@H]2C1=CC(OC)=C(O)C(OC)=C1
InChI IdentifierInChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m0/s1
InChI KeyKOWMJRJXZMEZLD-HCIHMXRSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative Parents
Substituents
  • Furanoid lignan
  • Furofuran lignan skeleton
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Furofuran
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility0.048 g/LALOGPS
logP2.23ALOGPS
logP1.96ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.03 m³·mol⁻¹ChemAxon
Polarizability41.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-1eddaadd010301136dbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-95e01861e7425e989fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5910000000-033b80fab83d960dd4acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-5a6d1665f8ea4a163f32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-d2993b0ccead22d975f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2936000000-e9d278bf1b5e16bef9caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0021900000-fafdeccda01e4a579654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0257900000-8631f217fe0c73e1ae11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-0294100000-724a71a5291f8daf0612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-123dc6784d974ffacb59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0009500000-a0c6565e7c694745a70dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014v-0259500000-e9fda1d76d73c29a9152Spectrum
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 IDHMDB0303494
FooDB IDFDB014720
Phenol Explorer IDNot Available
KNApSAcK IDC00002631
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID391324
ChEBI ID47
PubChem Compound ID443023
Kegg Compound IDC10889
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21500777