AFCDB: (8R,8'R)-Secoisolariciresinol (FDB021314)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:37 UTC

Update date

2019-11-26 03:20:11 UTC

Primary ID

FDB021314

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(8R,8'R)-Secoisolariciresinol

Description

Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, 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 grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. 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 Number

29388-59-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	2.05	ALOGPS
logP	2.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	99.29 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H26O6

IUPAC name

(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

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 Key

PUETUDUXMCLALY-HOTGVXAUSA-N

Isomeric SMILES

COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1

Average Molecular Weight

362.4168

Monoisotopic Molecular Weight

362.172938564

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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

secoisolariciresinol (CHEBI:65004 )
Lignans (C18167 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 66.28%; H 7.23%; O 26.49%	DFC
Melting Point	Mp 112-114°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D -32 (c, 1 in Me2CO)	DFC
Spectroscopic UV Data	282 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(+)-Secoisolariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001r-0905000000-3c10a7ce80aa82270fdf	Spectrum
Predicted GC-MS	(+)-Secoisolariciresinol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-7222129000-4a15ee9d5480cd864709	Spectrum
Predicted GC-MS	(+)-Secoisolariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-Secoisolariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-0931000000-1875abcf0a77c29ef991	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0931000000-1875abcf0a77c29ef991	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0079-1900000000-388f0c7eb9705dc8b6bd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0910000000-260d238ae45a244f9000	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0923000000-8b6573966f9f0d0dc18e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-1c5c1767a5d18a1ce39b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0923000000-d1247d61323b3bb185a1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0079-1900000000-0dd02f8018fd55488472	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-010c-2900000000-36ffcea5d0b4db42ec25	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0921000000-428dc5bb31028e4394cf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-7060ec03d70103514c76	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0429000000-83bec5092dea63cd01c0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0009000000-87492c20c18d06242b0a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0079-1900000000-f8cde078d6625c8f94eb	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0119000000-3af20da7d20bab27dd05	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01tj-0749000000-cfac94ec5340c6222037	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-0894000000-598931011d02757fdeba	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-bb339709d3dc1a17e110	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-bd59bd756314c4c5af52	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0349000000-ab9158c58cc922e633dd	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-55f1e5434dd9fb2f906e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-0009000000-7e6fdc2276121d8b599c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-0459000000-a7a975e7dbb9db40e2b3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0229000000-7b1b915316723c3b027a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ads-0869000000-e600d806308ccec4045c	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

65373

Pubchem Substance ID

Not Available

ChEBI ID

562878

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HJP59-C:NQS36-T

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00000604

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Secoisolariciresinol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

(8R,8'R)-Secoisolariciresinol (FDB021314)

Structure for FDB021314 ((8R,8'R)-Secoisolariciresinol)