(8R,8'R)-Secoisolariciresinol (CHEM034496)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:57:37 UTC
Update Date2016-11-09 01:21:08 UTC
Accession NumberCHEM034496
Identification
Common Name(8R,8'R)-Secoisolariciresinol
ClassSmall Molecule
DescriptionAn enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-SecoisolariciresinolKegg
2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediolMeSH
KnotolanMeSH
Secoisolariciresinol, (r*,s*)-isomerMeSH
SecoisolariciresinolChEBI
(8R,8'R)-(-)-SecoisolariciresinolPhytoBank
(8R,8’R)-(-)-SecoisolariciresinolPhytoBank
seco-IsolariciresinolPhytoBank
2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediolPhytoBank
2,3-Divanillyl-1,4-butanediolPhytoBank
Chemical FormulaC20H26O6
Average Molecular Mass362.417 g/mol
Monoisotopic Mass362.173 g/mol
CAS Registry Number29388-59-8
IUPAC Name(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Traditional Namesecoisolariciresinol
SMILESCOC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1
InChI IdentifierInChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
InChI KeyPUETUDUXMCLALY-HOTGVXAUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassDibenzylbutanediol lignans
Direct ParentDibenzylbutanediol lignans
Alternative Parents
Substituents
  • Dibenzylbutanediol
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.012 g/LALOGPS
logP2.05ALOGPS
logP2.33ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity99.29 m³·mol⁻¹ChemAxon
Polarizability38.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0905000000-3c10a7ce80aa82270fdfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000i-7222129000-4a15ee9d5480cd864709Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0931000000-1875abcf0a77c29ef991Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0931000000-1875abcf0a77c29ef991Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0079-1900000000-388f0c7eb9705dc8b6bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0910000000-260d238ae45a244f9000Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0923000000-8b6573966f9f0d0dc18eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-1c5c1767a5d18a1ce39bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0923000000-d1247d61323b3bb185a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0079-1900000000-0dd02f8018fd55488472Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-010c-2900000000-36ffcea5d0b4db42ec25Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921000000-428dc5bb31028e4394cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-7060ec03d70103514c76Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0429000000-83bec5092dea63cd01c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0009000000-87492c20c18d06242b0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0079-1900000000-f8cde078d6625c8f94ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0119000000-3af20da7d20bab27dd05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-0749000000-cfac94ec5340c6222037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0894000000-598931011d02757fdebaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-bb339709d3dc1a17e110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-bd59bd756314c4c5af52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0349000000-ab9158c58cc922e633ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-55f1e5434dd9fb2f906eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0009000000-7e6fdc2276121d8b599cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0459000000-a7a975e7dbb9db40e2b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0229000000-7b1b915316723c3b027aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ads-0869000000-e600d806308ccec4045cSpectrum
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 IDDB12179
HMDB IDHMDB0013692
FooDB IDFDB021314
Phenol Explorer IDNot Available
KNApSAcK IDC00000604
BiGG IDNot Available
BioCyc IDCPD-8909
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSecoisolariciresinol
Chemspider ID58845
ChEBI ID65004
PubChem Compound ID65373
Kegg Compound IDC18167
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15653677
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21837520
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21897049
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21958542
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22030618
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22037685
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22476613
8. Abarzua S, Serikawa T, Szewczyk M, Richter DU, Piechulla B, Briese V: Antiproliferative activity of lignans against the breast carcinoma cell lines MCF 7 and BT 20. Arch Gynecol Obstet. 2012 Apr;285(4):1145-51. doi: 10.1007/s00404-011-2120-6. Epub 2011 Oct 30.