ChemFOnt: Showing chemical card for 1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (CFc000160276)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:48:45 UTC

Chemfont ID

CFc000160276

Molecule Identification

Common Name

1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Definition

4-O-Feruloylquinic acid, also known as 4-O-feruloylquinate, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 4-O-Feruloylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-Feruloylquinate	Generator
1,3,5-Trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	Generator

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.338

Monoisotopic Molecular Weight

368.110732224

IUPAC Name

1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C(=O)OC1C(O)CC(O)(CC1O)C(O)=O

InChI Identifier

InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-15-11(19)7-17(24,16(22)23)8-12(15)20/h2-6,11-12,15,18-20,24H,7-8H2,1H3,(H,22,23)/b5-3+

InChI Key

VTMFDSJJVNQXLT-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Styrene
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Carboxylic acid
Ether
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.8 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.12	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.72 m³·mol⁻¹	ChemAxon
Polarizability	35.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0179868

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

6171347

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (CFc000160276)

MOL for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D MOL for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D SDF for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D-SDF for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

PDB for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D PDB for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

SMILES for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

INCHI for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

Structure for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D Structure for CFc000160276 (1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)