ChemFOnt: Showing chemical card for (+)-Syringaresinol (CFc000283010)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:53 UTC

Chemfont ID

CFc000283010

Molecule Identification

Common Name

(+)-Syringaresinol

Definition

(+)-syringaresinol is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-syringaresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-syringaresinol can be found in a number of food items such as radish (variety), grape wine, oat, and ginkgo nuts, which makes (+)-syringaresinol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,4'-(1S,3AR,4S,6ar)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)	ChEBI
Syringa-resinol	MeSH
Syringaresinol	MeSH
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomer	MeSH
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomer	MeSH
(+)-Lirioresinol B	PhytoBank
(+)-Syringaresinol	PhytoBank
(±)-Syringaresinol	PhytoBank
dl-Syringaresinol	PhytoBank

Chemical Formula

C₂₂H₂₆O₈

Average Molecular Weight

418.437

Monoisotopic Molecular Weight

418.162767808

IUPAC Name

4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

Traditional Name

(+)-syringaresinol

CAS Registry Number

21453-69-0

SMILES

[H][C@]12CO[C@H](C3=CC(OC)=C(O)C(OC)=C3)[C@@]1([H])CO[C@@H]2C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m0/s1

InChI Key

KOWMJRJXZMEZLD-HCIHMXRSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Furofuran
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

syringaresinol (CHEBI:47 )
Lignans (C10889 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303494)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Tropical fruit

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Garden tomato (var.) (FooDB: FOOD00173)

Root vegetable

Black salsify (FooDB: FOOD00599)
Radish (var.) (FooDB: FOOD00263)

Cereal and cereal product

Cereal

Cereal product

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Tofu (FooDB: FOOD00696)

Gourd

Cucumber (FooDB: FOOD00065)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)
Sesame (FooDB: FOOD00170)

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Ginkgo nuts (FooDB: FOOD00367)
Quinoa (FooDB: FOOD00441)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Process

Not Available

Role

Biological role

Anti neoplastic (HMDB: HMDB0303494)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.23	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.03 m³·mol⁻¹	ChemAxon
Polarizability	41.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0303494

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443023

PDB ID

Not Available

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (+)-Syringaresinol (CFc000283010)

MOL for CFc000283010 ((+)-Syringaresinol)

3D MOL for CFc000283010 ((+)-Syringaresinol)

3D SDF for CFc000283010 ((+)-Syringaresinol)

3D-SDF for CFc000283010 ((+)-Syringaresinol)

PDB for CFc000283010 ((+)-Syringaresinol)

3D PDB for CFc000283010 ((+)-Syringaresinol)

SMILES for CFc000283010 ((+)-Syringaresinol)

INCHI for CFc000283010 ((+)-Syringaresinol)

Structure for CFc000283010 ((+)-Syringaresinol)

3D Structure for CFc000283010 ((+)-Syringaresinol)