Secoisolariciresinol (CED0005966)

Record Information
Version1.0
Creation Date2016-05-26 00:24:34 UTC
Update Date2026-04-03 21:15:52 UTC
SynCED IDCED0005966
Secondary Accession Numbers
  • CHEM028368
Identification
Common NameSecoisolariciresinol
ClassSmall Molecule
Description
Secoisolariciresinol is an organic compound with the chemical formula C20H26O6 and an average molecular weight of 362.42 g/mol. Secoisolariciresinol belongs to the dibenzylbutanediol lignans, a subclass of dibenzylbutane lignans within the organic compounds. This compound has been identified in three recorded sources. It is associated with food, food processing, and cookware, specifically in the preparation of vinegar and the preparation of wort. Additionally, it is found in household cleaning and consumer products, specifically in cigar cigarettes.
Contaminant Type
  • Phenolic Antioxidant
Chemical Structure
SynonymsNot Available
Chemical FormulaC20H26O6
Average Molecular Mass362.417 g/mol
Monoisotopic Mass362.173 g/mol
CAS Registry Number29388-59-8
IUPAC Name2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Traditional Namesecoisolariciresinol
SMILESCOC1=CC(CC(CO)C(CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O
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
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
Polarizability38.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001r-1915000000-8f21ac6886342fec0b8aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-86a19cceb765363c6c3dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0409000000-eeec87a5d05d8cad84b6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0409000000-d28269e60145cdf968b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0923000000-e3cd4574085ad0b99441Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0219000000-692a1c9d2eddb5dbf93cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0900000000-0aa6c9f2d0f95c1771eaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0619000000-7eb65b8946da939e6aafNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0509000000-6307ad0eeabdf74faadeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-f991b4d8aa0bc41a2bb8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-7b15127eb1b7d2a7c692Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0009000000-3412a478cd376c36c624Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0932000000-e95f792f354628352a01Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0900000000-e4b30615a185daf1408fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0900000000-3ddae6c789582868ce1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0923000000-8b6573966f9f0d0dc18eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-0119000000-1cdc86caf972b10c304aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01tj-0749000000-7e29d88c1ab14761cc4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ap0-0894000000-3d2652e6b90bdd716e7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-0119000000-1cdc86caf972b10c304aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01tj-0749000000-7e29d88c1ab14761cc4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ap0-0894000000-3d2652e6b90bdd716e7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-f4e5ffd45d7cd71a3209Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-02a4ba9c95acb533e045Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0339000000-3eb29115c82617367816Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-f4e5ffd45d7cd71a3209Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-02a4ba9c95acb533e045Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0339000000-3eb29115c82617367816Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0249000000-7a8e384dcb8ff2798605Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05br-0769000000-6400934e46844d1ea389Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0953000000-84670b28f2093f6cc902Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-c9183f32c78ffbeef93eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-28ec36daef7f65a7521aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-0459000000-3e0ea5968d1d7856dac0Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
2547.0 Log mg/kg [1400:4500]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
gliomaAssociated With?Not AvailableNot AvailablePMC1513391
Exposure Sources
Source IDSourceSectorReference
CEDs000491Industrial manufacturing & chemical processingNot Available
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000548Preparation Of Vinegar?Vinegar is produced through the fermentation of ethanol by acetic acid bacteria, resulting in a solution that typically contains 4-8% acetic acid.Food, food processing & cookwarePubChem
CEDs000550Preparation Of Wort?The preparation of wort involves the extraction of sugars from malted grains, a crucial step in the brewing process.Food, food processing & cookwarePubChem
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000606Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.Agriculture & land managementPubChem
CEDs000609Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.Personal care & cosmeticsPubChem
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000614Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000617Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000618Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.Personal care & cosmeticsPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000738Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.Industrial manufacturing & chemical processingPubChem
CEDs000740Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.Paper, pulp & fiber productsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs01157FoodsFood, food processing & cookwarePMC7731202 , PMC7731202
CEDs01160CerealsFood, food processing & cookwarePMC8320611
CEDs01483Processed Food ProductsFood, food processing & cookwarePMC8320611
Pathways
0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansKnownNot Available
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)
Prediction Confidence Score
0.419
Applicability Domain
0.5
Statistical Significance
0.002
Supporting Reference Compounds
182
E-value
15.492
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)
Prediction Confidence Score
0.413
Applicability Domain
0.697
Statistical Significance
5.10e-04
Supporting Reference Compounds
60
E-value
3.97031
Carbonic anhydrase structureClick to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)
Prediction Confidence Score
0.413
Applicability Domain
0.697
Statistical Significance
7.40e-04
Supporting Reference Compounds
68
E-value
5.76084
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)
Prediction Confidence Score
0.408
Applicability Domain
0.435
Statistical Significance
0.0158
Supporting Reference Compounds
1245
E-value
123.391
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)
Prediction Confidence Score
0.406
Applicability Domain
0.697
Statistical Significance
9.60e-04
Supporting Reference Compounds
38
E-value
7.47353
Click to view 3D structure17-beta-hydroxysteroid dehydrogenase type 2P37059HumansPredicted (SEA)
Prediction Confidence Score
0.402
Applicability Domain
0.697
Statistical Significance
6.30e-04
Supporting Reference Compounds
44
E-value
4.9045
Beta-carbonic anhydrase 1 structureClick to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)
Prediction Confidence Score
0.4
Applicability Domain
0.697
Statistical Significance
0.0013
Supporting Reference Compounds
55
E-value
10.1982
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P16050HumansPredicted (SEA)
Prediction Confidence Score
0.398
Applicability Domain
0.639
Statistical Significance
1.50e-04
Supporting Reference Compounds
46
E-value
1.16774
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)
Prediction Confidence Score
0.37
Applicability Domain
0.435
Statistical Significance
1.00e-03
Supporting Reference Compounds
150
E-value
7.78492
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)
Prediction Confidence Score
0.37
Applicability Domain
0.435
Statistical Significance
0.0047
Supporting Reference Compounds
305
E-value
36.5891
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)
Prediction Confidence Score
0.368
Applicability Domain
0.435
Statistical Significance
0.0161
Supporting Reference Compounds
793
E-value
125.493
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)
Prediction Confidence Score
0.357
Applicability Domain
0.417
Statistical Significance
4.40e-04
Supporting Reference Compounds
38
E-value
3.42537
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)
Prediction Confidence Score
0.356
Applicability Domain
0.395
Statistical Significance
0.0119
Supporting Reference Compounds
372
E-value
92.3292
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)
Prediction Confidence Score
0.354
Applicability Domain
0.435
Statistical Significance
0.0192
Supporting Reference Compounds
825
E-value
149.393
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)
Prediction Confidence Score
0.353
Applicability Domain
0.395
Statistical Significance
0.0055
Supporting Reference Compounds
109
E-value
43.1285
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)
Prediction Confidence Score
0.352
Applicability Domain
0.395
Statistical Significance
0.0119
Supporting Reference Compounds
332
E-value
92.3292
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)
Prediction Confidence Score
0.351
Applicability Domain
0.395
Statistical Significance
0.0081
Supporting Reference Compounds
242
E-value
63.0579
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)
Prediction Confidence Score
0.346
Applicability Domain
0.395
Statistical Significance
0.0047
Supporting Reference Compounds
151
E-value
36.7448
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)
Prediction Confidence Score
0.344
Applicability Domain
0.395
Statistical Significance
0.0613
Supporting Reference Compounds
1301
E-value
477.371
17-beta-hydroxysteroid dehydrogenase type 1 structureClick to view 3D structure17-beta-hydroxysteroid dehydrogenase type 1P14061HumansPredicted (SEA)
Prediction Confidence Score
0.343
Applicability Domain
0.697
Statistical Significance
0.0012
Supporting Reference Compounds
42
E-value
9.49761
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)
Prediction Confidence Score
0.342
Applicability Domain
0.404
Statistical Significance
0.0632
Supporting Reference Compounds
1538
E-value
492.396
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)
Prediction Confidence Score
0.342
Applicability Domain
0.395
Statistical Significance
0.0194
Supporting Reference Compounds
472
E-value
150.716
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)
Prediction Confidence Score
0.336
Applicability Domain
0.395
Statistical Significance
0.0187
Supporting Reference Compounds
407
E-value
145.734
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)
Prediction Confidence Score
0.332
Applicability Domain
0.395
Statistical Significance
0.0026
Supporting Reference Compounds
29
E-value
19.9294
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)
Prediction Confidence Score
0.332
Applicability Domain
0.372
Statistical Significance
0.0082
Supporting Reference Compounds
172
E-value
63.6028
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0252297
FooDB IDFDB012660
Phenol Explorer IDNot Available
KNApSAcK IDC00000604
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSecoisolariciresinol
Chemspider ID509696
ChEBI IDNot Available
PubChem Compound ID586372
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available