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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:33 UTC
Update Date2021-09-14 14:57:21 UTC
HMDB IDHMDB0013692
Secondary Accession Numbers
  • HMDB13692
Metabolite Identification
Common NameSecoisolariciresinol
DescriptionSecoisolariciresinol, also known as knotolan, belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol has been detected, but not quantified in, several different foods, such as cocoa beans (Theobroma cacao), swiss chards (Beta vulgaris ssp. cicla), tartary buckwheats (Fagopyrum tataricum), chanterelles (Cantharellus cibarius), and kohlrabis (Brassica oleracea var. gongylodes). This could make secoisolariciresinol a potential biomarker for the consumption of these foods. Secoisolariciresinol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Secoisolariciresinol.
Structure
Data?1601250629
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 Weight362.4168
Monoisotopic Molecular Weight362.172938564
IUPAC Name(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Traditional Namesecoisolariciresinol
CAS Registry Number29388-59-8
SMILES
COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.40931661259
DarkChem[M-H]-180.70631661259
DeepCCS[M+H]+189.99630932474
DeepCCS[M-H]-187.63830932474
DeepCCS[M-2H]-220.91130932474
DeepCCS[M+Na]+196.1430932474
AllCCS[M+H]+188.232859911
AllCCS[M+H-H2O]+185.132859911
AllCCS[M+NH4]+191.032859911
AllCCS[M+Na]+191.932859911
AllCCS[M-H]-189.632859911
AllCCS[M+Na-2H]-190.232859911
AllCCS[M+HCOO]-191.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SecoisolariciresinolCOC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C14946.0Standard polar33892256
SecoisolariciresinolCOC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C13234.4Standard non polar33892256
SecoisolariciresinolCOC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C13271.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Secoisolariciresinol,1TMS,isomer #1COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3142.6Semi standard non polar33892256
Secoisolariciresinol,1TMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O3098.7Semi standard non polar33892256
Secoisolariciresinol,2TMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3027.1Semi standard non polar33892256
Secoisolariciresinol,2TMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3026.0Semi standard non polar33892256
Secoisolariciresinol,2TMS,isomer #3COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C3080.0Semi standard non polar33892256
Secoisolariciresinol,2TMS,isomer #4COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O3033.5Semi standard non polar33892256
Secoisolariciresinol,3TMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O2968.8Semi standard non polar33892256
Secoisolariciresinol,3TMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C3006.6Semi standard non polar33892256
Secoisolariciresinol,4TMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C2997.1Semi standard non polar33892256
Secoisolariciresinol,1TBDMS,isomer #1COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3420.3Semi standard non polar33892256
Secoisolariciresinol,1TBDMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O3381.2Semi standard non polar33892256
Secoisolariciresinol,2TBDMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3564.3Semi standard non polar33892256
Secoisolariciresinol,2TBDMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3564.4Semi standard non polar33892256
Secoisolariciresinol,2TBDMS,isomer #3COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3624.1Semi standard non polar33892256
Secoisolariciresinol,2TBDMS,isomer #4COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O3577.3Semi standard non polar33892256
Secoisolariciresinol,3TBDMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3738.7Semi standard non polar33892256
Secoisolariciresinol,3TBDMS,isomer #2COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3746.4Semi standard non polar33892256
Secoisolariciresinol,4TBDMS,isomer #1COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3901.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0905000000-3c10a7ce80aa82270fdf2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Secoisolariciresinol GC-MS (4 TMS) - 70eV, Positivesplash10-000i-7222129000-4a15ee9d5480cd8647092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol LC-ESI-qTof , Positive-QTOFsplash10-000i-0931000000-1875abcf0a77c29ef9912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol , positive-QTOFsplash10-000i-0931000000-1875abcf0a77c29ef9912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOFsplash10-0079-1900000000-388f0c7eb9705dc8b6bd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOFsplash10-000i-0910000000-260d238ae45a244f90002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-000i-0923000000-8b6573966f9f0d0dc18e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOFsplash10-000i-0900000000-1c5c1767a5d18a1ce39b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-000i-0923000000-d1247d61323b3bb185a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOFsplash10-0079-1900000000-0dd02f8018fd554884722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOFsplash10-010c-2900000000-36ffcea5d0b4db42ec252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-000i-0921000000-428dc5bb31028e4394cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOFsplash10-000i-0900000000-7060ec03d70103514c762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-004i-0429000000-83bec5092dea63cd01c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 35V, Negative-QTOFsplash10-03di-0009000000-87492c20c18d06242b0a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Secoisolariciresinol 6V, Positive-QTOFsplash10-0079-1900000000-f8cde078d6625c8f94eb2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-03dj-0119000000-3af20da7d20bab27dd052017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Positive-QTOFsplash10-01tj-0749000000-cfac94ec5340c62220372017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Positive-QTOFsplash10-0a4r-0894000000-598931011d02757fdeba2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Negative-QTOFsplash10-03di-0009000000-bb339709d3dc1a17e1102017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Negative-QTOFsplash10-03di-0009000000-bd59bd756314c4c5af522017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Negative-QTOFsplash10-014i-0349000000-ab9158c58cc922e633dd2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Negative-QTOFsplash10-03di-0009000000-55f1e5434dd9fb2f906e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Negative-QTOFsplash10-02t9-0009000000-7e6fdc2276121d8b599c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Negative-QTOFsplash10-0aor-0459000000-a7a975e7dbb9db40e2b32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOFsplash10-03di-0229000000-7b1b915316723c3b027a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Positive-QTOFsplash10-0ads-0869000000-e600d806308ccec4045c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0400 +/- 0.0933 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12179
Phenol Explorer Compound IDNot Available
FooDB IDFDB021314
KNApSAcK IDC00000604
Chemspider ID58845
KEGG Compound IDC18167
BioCyc IDCPD-8909
BiGG IDNot Available
Wikipedia LinkSecoisolariciresinol
METLIN IDNot Available
PubChem Compound65373
PDB IDNot Available
ChEBI ID65004
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:22037685 ]