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Showing Compound Secoisolariciresinol (FDB012660)

Record Information
Version1.0
Creation date2010-04-08 22:10:17 UTC
Update date2025-11-18 23:38:37 UTC
Primary IDFDB012660
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSecoisolariciresinol
DescriptionSecoisolariciresinol is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as barley, wheat bread, broad bean, and poppy, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 % .
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol, 9CIdb_source
4,4',9,9'-Tetrahydroxy-3,3'-dimethoxylignandb_source
seco-Isolariciresinoldb_source
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
Polarizability38.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26O6
IUPAC name2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
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
InChI KeyPUETUDUXMCLALY-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC(CO)C(CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O
Average Molecular Weight362.4168
Monoisotopic Molecular Weight362.172938564
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.28%; H 7.23%; O 26.49%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSecoisolariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001r-1915000000-8f21ac6886342fec0b8aSpectrum
Predicted GC-MSSecoisolariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSecoisolariciresinol, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-1900000000-86a19cceb765363c6c3d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-03di-0409000000-eeec87a5d05d8cad84b62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0409000000-d28269e60145cdf968b52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0923000000-e3cd4574085ad0b994412021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0219000000-692a1c9d2eddb5dbf93c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00xr-0900000000-0aa6c9f2d0f95c1771ea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0619000000-7eb65b8946da939e6aaf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0509000000-6307ad0eeabdf74faade2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0900000000-f991b4d8aa0bc41a2bb82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-1900000000-7b15127eb1b7d2a7c6922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0009000000-3412a478cd376c36c6242021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-0932000000-e95f792f354628352a012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00xr-0900000000-e4b30615a185daf1408f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0119000000-1cdc86caf972b10c304a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-0749000000-7e29d88c1ab14761cc4b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-0894000000-3d2652e6b90bdd716e7d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0119000000-1cdc86caf972b10c304a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-0749000000-7e29d88c1ab14761cc4b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-0894000000-3d2652e6b90bdd716e7d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-f4e5ffd45d7cd71a32092015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-02a4ba9c95acb533e0452015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0339000000-3eb29115c826173678162015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-f4e5ffd45d7cd71a32092015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-02a4ba9c95acb533e0452015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0339000000-3eb29115c826173678162015-05-27View Spectrum
NMRNot Available
ChemSpider ID509696
ChEMBL IDCHEMBL476284
KEGG Compound IDNot Available
Pubchem Compound ID586372
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID594
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHJP59-C:HJP59-C
EAFUS IDNot Available
Dr. Duke IDSECOISOLARICIRESINOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSecoisolariciresinol
Phenol-Explorer Metabolite ID594
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Aromatase inhibitor50790 An agent that blocks the activity of aromatase, an enzyme converting androgens to estrogens, reducing estrogen levels. Therapeutically, it's used to treat hormone-sensitive breast cancer, endometriosis, and infertility, by decreasing estrogen-dependent growth and symptoms.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).