AFCDB: (-)-Pinoresinol (FDB001440)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:58 UTC

Update date

2019-11-26 02:56:28 UTC

Primary ID

FDB001440

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-Pinoresinol

Description

(-)-pinoresinol is a member of the class of compounds known as lignan glycosides. Lignan glycosides are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones (-)-pinoresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-pinoresinol can be found in a number of food items such as java plum, peach, soursop, and oregon yampah, which makes (-)-pinoresinol a potential biomarker for the consumption of these food products (-)-pinoresinol is a lignan found in Styrax species and in Forsythia suspensa. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants .

CAS Number

81446-29-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.0097	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.24 m³·mol⁻¹	ChemAxon
Polarizability	53.26 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C26H32O11

IUPAC name

(2S,3R,4S,5S,6R)-2-{4-[(1R,3aS,4R,6aS)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3/t14-,15-,20-,21-,22+,23-,24+,25+,26-/m1/s1

InChI Key

QLJNETOQFQXTLI-JKUDBEEXSA-N

Isomeric SMILES

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

Average Molecular Weight

520.5257

Monoisotopic Molecular Weight

520.194461866

Classification

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Methoxybenzene
Furofuran
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Dialkyl ether
Ether
Acetal
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glycoside (CHEBI:81162 )
lignan (CHEBI:81162 )
Lignan glycosides (C17529 )

Ontology

No ontology term

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	splash10-0ab9-0109050000-f95626158e89f1f84c3d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0129000000-d0defe6f3fd203f7a47b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2920000000-c09d174487f5bf74857e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-066r-2306090000-866f1a12a36be1f4b072	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-1209110000-a3202f8a52387e964f40	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-3529000000-0c99c155afff2436260d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0112090000-ea588e0f1a3564065d5d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kms-1149360000-2da464f87d53b79f5ccf	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-5208910000-f593f3b6a112e12f5f8f	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-fe279838b7497ff13d42	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ldl-3105690000-9a84ba2f03cb131948ca	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-2335290000-020cdc12bd6369011aba	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C17529

Pubchem Compound ID

25245730

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

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

C00000587

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

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.

(-)-Pinoresinol (FDB001440)

Structure for FDB001440 ((-)-Pinoresinol)