ChemFOnt: Showing chemical card for 1,5-Diferuloylquinic acid (CFc000022503)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:51 UTC

Chemfont ID

CFc000022503

Molecule Identification

Common Name

1,5-Diferuloylquinic acid

Definition

1,5-Diferuloylquinic acid is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,5-Diferuloylquinate	Generator
(1R,3R,4S,5R)-3,4-Dihydroxy-1,5-bis({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy})cyclohexane-1-carboxylate	HMDB

Chemical Formula

C₂₇H₂₈O₁₂

Average Molecular Weight

544.504

Monoisotopic Molecular Weight

544.15807636

IUPAC Name

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

Traditional Name

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

CAS Registry Number

None

SMILES

COC1=CC(\C=C\C(=O)O[C@@]2(C[C@@H](O)[C@H](O)[C@@H](C2)OC(=O)\C=C\C2=CC(OC)=C(O)C=C2)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C27H28O12/c1-36-20-11-15(3-7-17(20)28)5-9-23(31)38-22-14-27(26(34)35,13-19(30)25(22)33)39-24(32)10-6-16-4-8-18(29)21(12-16)37-2/h3-12,19,22,25,28-30,33H,13-14H2,1-2H3,(H,34,35)/b9-5+,10-6+/t19-,22-,25+,27-/m1/s1

InChI Key

YSOVEZGZSWEECD-HPMQQOSDSA-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
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Phenol ether
Anisole
Styrene
Methoxybenzene
Cyclohexanol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
1,2-diol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxide
Carbonyl group
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: HMDB0041641)
Cell membrane (HMDB: HMDB0041641)

Source

Exogenous

Exogenous (HMDB: HMDB0041641)

Food

Food (HMDB: HMDB0041641)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041641)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.45	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	135.73 m³·mol⁻¹	ChemAxon
Polarizability	54.4 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

HMDB0041641

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029796

KNApSAcK ID

Not Available

Chemspider ID

30777583

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753172

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1,5-Diferuloylquinic acid (CFc000022503)

MOL for CFc000022503 (1,5-Diferuloylquinic acid)

3D MOL for CFc000022503 (1,5-Diferuloylquinic acid)

3D SDF for CFc000022503 (1,5-Diferuloylquinic acid)

3D-SDF for CFc000022503 (1,5-Diferuloylquinic acid)

PDB for CFc000022503 (1,5-Diferuloylquinic acid)

3D PDB for CFc000022503 (1,5-Diferuloylquinic acid)

SMILES for CFc000022503 (1,5-Diferuloylquinic acid)

INCHI for CFc000022503 (1,5-Diferuloylquinic acid)

Structure for CFc000022503 (1,5-Diferuloylquinic acid)

3D Structure for CFc000022503 (1,5-Diferuloylquinic acid)