ChemFOnt: Showing chemical card for Valoneic acid dilactone (CFc000281223)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:24 UTC

Chemfont ID

CFc000281223

Molecule Identification

Common Name

Valoneic acid dilactone

Definition

Valoneic acid dilactone is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Valoneic acid dilactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Valoneic acid dilactone can be found in cloves, common walnut, and japanese walnut, which makes valoneic acid dilactone a potential biomarker for the consumption of these food products. Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laeviforia and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur) .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Valoneate dilactone	Generator

Chemical Formula

C₂₁H₁₀O₁₃

Average Molecular Weight

470.298

Monoisotopic Molecular Weight

470.012140382

IUPAC Name

3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid

Traditional Name

3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid

CAS Registry Number

None

SMILES

OC(=O)C1=C(OC2=C(O)C3=C4C(=C2)C(=O)OC2=C(O)C(O)=CC(C(=O)O3)=C42)C(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)

InChI Key

BPAOAXAAABIQKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
7,8-dihydroxycoumarin
Gallic acid or derivatives
Gallic acid
Isocoumarin
Diaryl ether
Coumarin
Hydroxybenzoic acid
Benzopyran
1-benzopyran
2-benzopyran
Benzenetriol
Benzoic acid or derivatives
Benzoic acid
Pyrogallol derivative
Phenol ether
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Ether
Polyol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301707)

Food

Herb and spice

Spice

Cloves (FooDB: FOOD00179)

Nut

Common walnut (FooDB: FOOD00094)
Japanese walnut (FooDB: FOOD00240)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.87	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.07 m³·mol⁻¹	ChemAxon
Polarizability	40.96 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000230

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valoneic acid dilactone

METLIN ID

Not Available

PubChem Compound

10151874

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Valoneic acid dilactone (CFc000281223)

MOL for CFc000281223 (Valoneic acid dilactone)

3D MOL for CFc000281223 (Valoneic acid dilactone)

3D SDF for CFc000281223 (Valoneic acid dilactone)

3D-SDF for CFc000281223 (Valoneic acid dilactone)

PDB for CFc000281223 (Valoneic acid dilactone)

3D PDB for CFc000281223 (Valoneic acid dilactone)

SMILES for CFc000281223 (Valoneic acid dilactone)

INCHI for CFc000281223 (Valoneic acid dilactone)

Structure for CFc000281223 (Valoneic acid dilactone)

3D Structure for CFc000281223 (Valoneic acid dilactone)