Lirioresinol A (CHEM032265)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:15:53 UTC
Update Date2016-11-09 01:19:26 UTC
Accession NumberCHEM032265
Identification
Common NameLirioresinol A
ClassSmall Molecule
DescriptionA lignan that is 7,9':7',9-diepoxylignane substituted by hydroxy groups at positions 4 and 4' and methoxy groups at positions 3, 3', 5 and 5' respectively.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,4'-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)ChEBI
S(8-8)SChEBI
(+)-EpisyringaresinolHMDB
SymplicosigenolHMDB
SyringaresinolMeSH, HMDB
Syringa-resinolMeSH, HMDB
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomerMeSH, HMDB
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomerMeSH, HMDB
Chemical FormulaC22H26O8
Average Molecular Mass418.437 g/mol
Monoisotopic Mass418.163 g/mol
CAS Registry Number21453-71-4
IUPAC Name4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
Traditional Namesyringaresinol
SMILESCOC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=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
InChI KeyKOWMJRJXZMEZLD-UHFFFAOYSA-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
Polarizability43 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00li-1982000000-33ff9b96f717a6cbdd51Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052b-2096070000-90aaa198754bac5787a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-2859d81bb81159bc981bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0133900000-8d3f30e7c98a7d4d07aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-0496200000-297522aaeb8abe2e99adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-123dc6784d974ffacb59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0039200000-0a5b58078e104a129859Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0092200000-6ede323068b3f2abe115Spectrum
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 IDHMDB0038928
FooDB IDFDB018395
Phenol Explorer ID598
KNApSAcK IDC00053808
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID90423
ChEBI ID49211
PubChem Compound ID100067
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=11152952
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12081149
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22170035
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25415049
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25479772
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=27450788
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=27976725
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28045228
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.