Showing Compound 1,5-Dicaffeoylquinic acid (FDB001514)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:00 UTC

Update date

2020-02-24 19:10:23 UTC

Primary ID

FDB001514

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1,5-Dicaffeoylquinic acid

Description

1,5-Dicaffeoylquinic acid, also known as cynarin, 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. 1,5-Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,5-Dicaffeoylquinic acid has been detected, but not quantified in, a few different foods, such as cardoons, fennels, and globe artichokes. This could make 1,5-dicaffeoylquinic acid a potential biomarker for the consumption of these foods.

CAS Number

30964-13-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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

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

Chemical Formula

C25H24O12

IUPAC name

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

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

Isomeric 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

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03dl-8592200000-bf336f61df2036277f1e	Spectrum
Predicted GC-MS	1,5-Dicaffeoylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-8592200000-bf336f61df2036277f1e	Spectrum
Predicted GC-MS	1,5-Dicaffeoylquinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-1945103000-92e839d6fb722a93bc0b	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02tj-0709640000-93a124ca1ee347170ee5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0907300000-c1b3f5ea82ad93560c14	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-024u-0902200000-aeb4454f422056c292f4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0419580000-83812afaf2e5ea383af6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r99-0729300000-eba47ae47a52917059ab	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06vi-0915000000-c68bce1e5294ad4dca56	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xs-0905430000-e56ccef26012aa1a2752	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0901100000-039532264a956bcc1b1c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0409-1900200000-b1fdfb3ba1ae534a6395	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0200090000-b7b5c2bba6df98a0de34	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0948000000-1aadf69ab983a16d0ff7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0921100000-a6f3439fcc24a437a7db	Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

528

DrugBank ID

Not Available

HMDB ID

HMDB30093

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CYNARIN

BIGG ID

Not Available

KNApSAcK ID

C00002733

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Cynarine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dyspeptic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti lipolytic			DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti sunburn	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cholagogue			DUKE
choleretic			DUKE
cholesterolytic			DUKE
central nervous system active	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
collagen-sparing			DUKE
cytoprotective			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hepatoregenerative	62868	Any compound that is able to prevent damage to the liver.	DUKE
hepatotonic			DUKE
hyperemic			DUKE
hypocholesterolemic			DUKE
hypolipidemic			DUKE
hypotriglyceridemic			DUKE
lipolytic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE