ChemFOnt: Showing chemical card for 8-8'-Dehydrodiferulic acid (CFc000010522)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:59 UTC

Chemfont ID

CFc000010522

Molecule Identification

Common Name

8-8'-Dehydrodiferulic acid

Definition

8-8'-Dehydrodiferulic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-8'-Dehydrodiferulate	Generator
(2E)-Bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate	HMDB

Chemical Formula

C₂₀H₁₈O₈

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

IUPAC Name

(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

Traditional Name

(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

CAS Registry Number

None

SMILES

COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1

InChI Identifier

InChI=1S/C20H18O8/c1-27-17-9-11(3-5-15(17)21)7-13(19(23)24)14(20(25)26)8-12-4-6-16(22)18(10-12)28-2/h3-10,21-22H,1-2H3,(H,23,24)(H,25,26)/b13-7-,14-8+

InChI Key

SPKZMOSDXTYXLK-MFUUIURDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029277)
Cell membrane (HMDB: HMDB0029277)

Source

Endogenous

Endogenous (HMDB: HMDB0029277)

Exogenous

Food

Food (HMDB: HMDB0029277)

Exogenous (HMDB: HMDB0029277)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	3.24	ALOGPS
logP	2.79	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.72 m³·mol⁻¹	ChemAxon
Polarizability	37.13 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

External Links

HMDB ID

HMDB0029277

DrugBank ID

Not Available

Phenol Explorer Compound ID

517

FooDB ID

FDB000272

KNApSAcK ID

Not Available

Chemspider ID

29336462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750840

PDB ID

Not Available

ChEBI ID

175914

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 8-8'-Dehydrodiferulic acid (CFc000010522)

MOL for CFc000010522 (8-8'-Dehydrodiferulic acid)

3D MOL for CFc000010522 (8-8'-Dehydrodiferulic acid)

3D SDF for CFc000010522 (8-8'-Dehydrodiferulic acid)

3D-SDF for CFc000010522 (8-8'-Dehydrodiferulic acid)

PDB for CFc000010522 (8-8'-Dehydrodiferulic acid)

3D PDB for CFc000010522 (8-8'-Dehydrodiferulic acid)

SMILES for CFc000010522 (8-8'-Dehydrodiferulic acid)

INCHI for CFc000010522 (8-8'-Dehydrodiferulic acid)

Structure for CFc000010522 (8-8'-Dehydrodiferulic acid)

3D Structure for CFc000010522 (8-8'-Dehydrodiferulic acid)