ChemFOnt: Showing chemical card for 6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000129237)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:58:05 UTC

Chemfont ID

CFc000129237

Molecule Identification

Common Name

6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

Aureusidin 6-glucuronide belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton. Thus, aureusidin 6-glucuronide is considered to be a flavonoid lipid molecule. Aureusidin 6-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₁₂

Average Molecular Weight

462.363

Monoisotopic Molecular Weight

462.07982602

IUPAC Name

6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

aureusidin 6-glucuronide

CAS Registry Number

Not Available

SMILES

OC1C(OC2=CC(O)=C3C(OC(=CC4=CC(O)=C(O)C=C4)C3=O)=C2)OC(C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)4-13-15(25)14-11(24)5-8(6-12(14)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)

InChI Key

FEUCUHLYVPMSHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Aurone O-glycosides

Alternative Parents

Substituents

Aurone-6-o-glycoside
Aurone
Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Catechol
Aryl ketone
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Hydroxy acid
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130035 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0148828)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	1.27	ALOGPS
logP	0.69	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.98 m³·mol⁻¹	ChemAxon
Polarizability	43.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0148828

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607767

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000129237)

MOL for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000129237 (6-({2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)