AFCDB: 7-Hydroxymatairesinol (FDB000325)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:31 UTC

Update date

2019-11-26 02:54:38 UTC

Primary ID

FDB000325

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

7-Hydroxymatairesinol

Description

7-hydroxymatairesinol is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 7-hydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-hydroxymatairesinol can be found in sesame, which makes 7-hydroxymatairesinol a potential biomarker for the consumption of this food product. Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro .

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	2	ALOGPS
logP	2.22	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97 m³·mol⁻¹	ChemAxon
Polarizability	38.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H22O7

IUPAC name

(4R)-3-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

InChI Identifier

InChI=1S/C20H22O7/c1-25-16-8-11(3-5-14(16)21)7-13-10-27-20(24)18(13)19(23)12-4-6-15(22)17(9-12)26-2/h3-6,8-9,13,18-19,21-23H,7,10H2,1-2H3/t13-,18?,19+/m0/s1

InChI Key

ZZSOKNNVDKKSDE-LPHKOSDUSA-N

Isomeric SMILES

COC1=CC(C[C@H]2COC(=O)C2[C@H](O)C2=CC=C(O)C(OC)=C2)=CC=C1O

Average Molecular Weight

374.3845

Monoisotopic Molecular Weight

374.136553058

Classification

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Aromatic alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pdi-0319000000-2aa39a15834561e84a07	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0936000000-18196c525b66c5f784f4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-1901000000-070fa63d30be923e3bf3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0029000000-01c9185eb76cc13701f0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05i0-0769000000-a71c0986d0d546e4d187	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fkl-1921000000-7932636a3c70c4735cc3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fb9-0449000000-9a9e409ba5653877161b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-0921000000-da495f04d0c89989bd07	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-7935000000-cc8407bc8b141127c37a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-7da310c862d162edf437	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-0379000000-9818018ba7c114b6f7ae	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-0948000000-b3703abd21e58b84255d	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

614

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00038321

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

Not Available

Phenol-Explorer Metabolite ID

614

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

— 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.

7-Hydroxymatairesinol (FDB000325)

Structure for FDB000325 (7-Hydroxymatairesinol)