ChemFOnt: Showing chemical card for 3-Caffeoyl-4-feruloylquinic acid (CFc000018028)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:08:17 UTC

Chemfont ID

CFc000018028

Molecule Identification

Common Name

3-Caffeoyl-4-feruloylquinic acid

Definition

3-Caffeoyl-4-feruloylquinic acid is found in citrus. 3-Caffeoyl-4-feruloylquinic acid is a constituent of the peel Citrus reticulata (mandarin).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Caffeoyl-4-feruloylquinate	Generator
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	HMDB

Chemical Formula

C₂₆H₂₆O₁₂

Average Molecular Weight

530.4774

Monoisotopic Molecular Weight

530.142426296

IUPAC Name

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

Traditional Name

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

CAS Registry Number

125132-81-2

SMILES

COC1=C(O)C=CC(\C=C/C(=O)OC2C(O)CC(O)(CC2OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C(O)=O)=C1

InChI Identifier

InChI=1S/C26H26O12/c1-36-20-11-15(3-7-17(20)28)5-9-23(32)38-24-19(30)12-26(35,25(33)34)13-21(24)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h2-11,19,21,24,27-30,35H,12-13H2,1H3,(H,33,34)/b8-4-,9-5-

InChI Key

RKAYMOSEFYVEJU-XEQVNJCQSA-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
Tricarboxylic acid or derivatives
Anisole
Catechol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Hydroxy acid
Fatty acyl
Benzenoid
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037092)
Cell membrane (HMDB: HMDB0037092)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037092)

Source

Exogenous

Exogenous (HMDB: HMDB0037092)

Food

Food (HMDB: HMDB0037092)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0037092)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037092)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.065 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.3	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.25 m³·mol⁻¹	ChemAxon
Polarizability	50.69 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

HMDB0037092

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016082

KNApSAcK ID

C00055232

Chemspider ID

35014368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752147

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Caffeoyl-4-feruloylquinic acid (CFc000018028)

MOL for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

3D MOL for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

3D SDF for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

3D-SDF for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

PDB for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

3D PDB for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

SMILES for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

INCHI for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

Structure for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)

3D Structure for CFc000018028 (3-Caffeoyl-4-feruloylquinic acid)