ChemFOnt: Showing chemical card for 6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000167187)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 00:00:58 UTC

Chemfont ID

CFc000167187

Molecule Identification

Common Name

6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 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. Based on a literature review very few articles have been published on 6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₂H₂₆O₁₅

Average Molecular Weight

530.435

Monoisotopic Molecular Weight

530.127170137

IUPAC Name

6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(OC2([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C2([H])O)=C(O)C=C1)C(=O)OC1([H])C[C@@](O)(CC([H])(O)C1([H])O)C(O)=O

InChI Identifier

InChI=1S/C22H26O15/c23-9-3-1-8(5-11(9)36-20-17(29)15(27)16(28)18(37-20)19(30)31)2-4-13(25)35-12-7-22(34,21(32)33)6-10(24)14(12)26/h1-5,10,12,14-18,20,23-24,26-29,34H,6-7H2,(H,30,31)(H,32,33)/b4-2+/t10?,12?,14?,15?,16?,17?,18?,20?,22-/m0/s1

InChI Key

XYKZOULGQZVNEK-AEYNZBPRSA-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
Glucuronic acid or derivatives
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Phenoxy compound
Styrene
Phenol ether
Beta-hydroxy acid
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyran
Monocyclic benzene moiety
Fatty acyl
Alpha-hydroxy acid
Benzenoid
Hydroxy acid
Cyclitol or derivatives
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.81 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	260.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	115.25 m³·mol⁻¹	ChemAxon
Polarizability	49.24 Å³	ChemAxon
Number of Rings	3	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

HMDB0186920

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000167187)

MOL for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000167187 (6-{5-[(1E)-3-{[(5S)-5-carboxy-2,3,5-trihydroxycyclohexyl]oxy}-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)