ChemFOnt: Showing chemical card for 1,5-Dicaffeoylquinic acid (CFc000011309)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:01 UTC

Chemfont ID

CFc000011309

Molecule Identification

Common Name

1,5-Dicaffeoylquinic acid

Definition

559

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cynarin	ChEBI
1,5-Dicaffeoylquinate	Generator
1,5-Di-O-caffeoylquinic acid	HMDB
Cinarine	HMDB
Cynarine	HMDB
1,3-Dicaffeoylquinate	Generator
Cinarin	MeSH
Cynarix	MeSH
Listrocol	MeSH
Phemocil	MeSH
1,5-Dicaffeoylquinic acid	MeSH
Nivellipid	MeSH
Cinarina	MeSH
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer	MeSH
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)	MeSH
Cynarex	MeSH
Listricol	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

IUPAC Name

(1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

cynarine

CAS Registry Number

30964-13-7

SMILES

O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

InChI Key

YDDUMTOHNYZQPO-RVXRWRFUSA-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
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quinic acid (CHEBI:520 )
alkyl caffeate ester (CHEBI:520 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030093)
Cytoplasm (HMDB: HMDB0030093)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030093)

Source

Endogenous

Endogenous (HMDB: HMDB0030093)

Plant

Plant (HMDB: HMDB0030093)

Exogenous

Food

Food (HMDB: HMDB0030093)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)
Cardoon (FooDB: FOOD00319)

Herb and spice

Herb

Fennel (FooDB: FOOD00082)

Exogenous (HMDB: HMDB0030093)

Process

Not Available

Role

Industrial application

Sweetening agent (HMDB: HMDB0030093)
Hepatoprotective agent (HMDB: HMDB0030093)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Diuretic (HMDB: HMDB0030093)

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0030093)

Agriculture

Pesticide (HMDB: HMDB0030093)

Biological role

Anti bacterial (HMDB: HMDB0030093)
Anti dyspeptic (HMDB: HMDB0030093)
Anti lipolytic (HMDB: HMDB0030093)
Anti staphylococcic (HMDB: HMDB0030093)
Anti streptococcic (HMDB: HMDB0030093)
Anti sunburn (HMDB: HMDB0030093)
Cholagogue (HMDB: HMDB0030093)
Choleretic (HMDB: HMDB0030093)
Cholesterolytic (HMDB: HMDB0030093)
Central nervous system active (HMDB: HMDB0030093)
Collagen-sparing (HMDB: HMDB0030093)
Cytoprotective (HMDB: HMDB0030093)
Hepatotonic (HMDB: HMDB0030093)
Hyperemic (HMDB: HMDB0030093)
Hypocholesterolemic (HMDB: HMDB0030093)
Hypolipidemic (HMDB: HMDB0030093)
Hypotriglyceridemic (HMDB: HMDB0030093)
Lipolytic (HMDB: HMDB0030093)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	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	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	50.19 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