Showing Compound (7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid (FDB021189)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:32 UTC

Update date

2019-11-26 03:20:01 UTC

Primary ID

FDB021189

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid

Description

3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 3-[3-carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid.

CAS Number

160169-55-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(7'R,8's)-4,7'-epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioate	Generator
(7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid	manual
3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoate	Generator
3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid, 9ci	HMDB
3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid, 9CI	db_source
5-(2-Carboxyvinyl)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-benzofurancarboxylic acid	HMDB
5-[(1Z)-2-Carboxyeth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylate	Generator

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.56	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.11 m³·mol⁻¹	ChemAxon
Polarizability	37.86 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

C20H18O8

IUPAC name

5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

InChI Identifier

InChI=1S/C20H18O8/c1-26-14-9-11(4-5-13(14)21)18-17(20(24)25)12-7-10(3-6-16(22)23)8-15(27-2)19(12)28-18/h3-9,17-18,21H,1-2H3,(H,22,23)(H,24,25)/b6-3-

InChI Key

JTHPLBUVRLOJBB-UTCJRWHESA-N

Isomeric SMILES

COC1=CC(\C=C/C(O)=O)=CC2=C1OC(C2C(O)=O)C1=CC(OC)=C(O)C=C1

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

Classification

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Coumaric acid or derivatives
Methoxyphenol
Benzofuran
Coumaran
Phenoxy compound
Methoxybenzene
Anisole
Styrene
Phenol ether
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Poaceae

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 62.18%; H 4.70%; O 33.13%	DFC
Melting Point	Mp 169-174° dec.	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	*(7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid, non-derivatized*, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kf-0309000000-3430f30bc375381be738	Spectrum
Predicted GC-MS	*(7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid, 3 TMS*, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-2000190000-2a741d2e3e25061bad43	Spectrum
Predicted GC-MS	*(7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid, non-derivatized*, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0109000000-e0b585f21780151fd3eb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gkc-0119000000-72f5f07bcc738dc87bdc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-1900000000-e3455fd2a3c777b30c17	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-0009000000-0e6a5f01ed2f3d7a4048	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mx-0019000000-e0de8b213dd69f233706	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-1649000000-3e0a5de588bcc30027c8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-26c5c39e4fb9c7194df2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0029000000-0a490dfde23643a97e74	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ar0-0194000000-d73bee2952709d583c42	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-5d1c4f43bb3b859a1786	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g6s-0039000000-7ea23dc0fa8f520267bf	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f7t-0976000000-c5327ce2cfcc3d97e270	2021-09-23	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

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB41277

CRC / DFC (Dictionary of Food Compounds) ID

MSK74-S:NMW05-B

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

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Food	Content Range	Average	Reference

Breakfast cereal	Expected but not quantified	Not Available	DFC CODES

Showing 1 to 1 of 1 entries

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

Showing Compound (7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid (FDB021189)

Structure for FDB021189 ((7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid)

Showing Compound (7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid (FDB021189)

Structure for FDB021189 ((7'R,8'S)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid)