ChemFOnt: Showing chemical card for 6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000114592)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:35:47 UTC

Chemfont ID

CFc000114592

Molecule Identification

Common Name

6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 4,5-dihydroxy-6-(hydroxymethyl)-2-(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 3,4,5-trihydroxybenzoate. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₆H₂₈O₂₀

Average Molecular Weight

660.49

Monoisotopic Molecular Weight

660.117393302

IUPAC Name

6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

OCC1OC(OC(=O)C2=CC(O)=C(O)C(OC3OC(C(O)C(O)C3O)C(O)=O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1O

InChI Identifier

InChI=1S/C26H28O20/c27-5-12-15(33)17(35)21(44-23(40)6-1-8(28)13(31)9(29)2-6)26(43-12)46-24(41)7-3-10(30)14(32)11(4-7)42-25-19(37)16(34)18(36)20(45-25)22(38)39/h1-4,12,15-21,25-37H,5H2,(H,38,39)

InChI Key

FMBBBKHAZREECR-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
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Galloyl ester
Glucuronic acid or derivatives
Gallic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Glycosyl compound
P-hydroxybenzoic acid alkyl ester
Dihydroxybenzoic acid
O-glycosyl compound
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Pyrogallol derivative
Phenoxy compound
Benzoyl
Catechol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Oxane
Monocyclic benzene moiety
Pyran
Benzenoid
Monosaccharide
Hydroxy acid
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carboxylic acid
Alcohol
Primary alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0134183)

Plant

Plant (HMDB: HMDB0134183)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.57 g/L	ALOGPS
logP	0.24	ALOGPS
logP	-1.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	340.12 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	139.46 m³·mol⁻¹	ChemAxon
Polarizability	59.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0134183

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB091199

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

131837924

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000114592)

MOL for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000114592 (6-[5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)