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 has been detected, but not quantified in, a few different foods, such as cardoons (Cynara cardunculus), fennels (Foeniculum vulgare), and globe artichokes (Cynara scolymus). This could make 1,5-dicaffeoylquinic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1,5-Dicaffeoylquinic acid.

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

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
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
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-6d52c792575df3ea7dbb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0903430000-a18151ab89b9b110f44c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-54c323557c7357c35524	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-1644d35ec69323eaa8a0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0uxr-0209050000-0f31371ea7d416714594	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0ufu-0904000000-2f7077d091afe3599b4f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-ae962c3fd60e067196d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-0900000000-51963ffb91ade18e9c29	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-002o-0900000000-f36e70eb02306a828238	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-002f-0900000000-cf7b0f27cf2a176d6f0e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02tj-0709640000-93a124ca1ee347170ee5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0907300000-c1b3f5ea82ad93560c14	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-024u-0902200000-aeb4454f422056c292f4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0419580000-83812afaf2e5ea383af6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r99-0729300000-eba47ae47a52917059ab	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06vi-0915000000-c68bce1e5294ad4dca56	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xs-0905430000-e56ccef26012aa1a2752	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0901100000-039532264a956bcc1b1c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0409-1900200000-b1fdfb3ba1ae534a6395	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0200090000-b7b5c2bba6df98a0de34	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0948000000-1aadf69ab983a16d0ff7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0921100000-a6f3439fcc24a437a7db	2021-09-23	View Spectrum

NMR

Not Available

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	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti dyspeptic	52217	An agent that alleviates indigestion and digestive discomfort, reducing symptoms of dyspepsia. It plays a biological role in regulating stomach acid and digestive enzyme activity. Therapeutically, it is used to manage gastrointestinal disorders, such as irritable bowel syndrome, and to relieve nausea, bloating, and abdominal pain. Key medical uses include treating gastroesophageal reflux disease and peptic ulcers.	DUKE
Anti lipolytic		An agent that prevents the breakdown of lipids, playing a biological role in regulating fat metabolism. Therapeutically, it is used to manage conditions like hypertriglyceridemia and diabetic ketoacidosis, with key medical applications in lipid disorders and cardiovascular disease prevention.	DUKE
Anti-staphylococcic	33282	An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.	DUKE
Anti-streptococcic	33282	An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.	DUKE
Anti sunburn	52217	An agent that protects the skin from sun damage, reducing inflammation and preventing burns. Its biological role is to absorb or reflect UV radiation, therapeutic applications include preventing skin cancer and photoaging, and key medical uses include treating sunburn, premature aging, and skin discoloration.	DUKE
Cholagogue		An agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Cholesterolytic		An enzyme that breaks down cholesterol, playing a key biological role in lipid metabolism. Therapeutically, it has applications in managing hypercholesterolemia and atherosclerosis, with potential uses in cardiovascular disease prevention and treatment.	DUKE
Central nervous system active	35470	An agent that affects brain and spinal cord function, influencing mood, cognition, and physical responses. Therapeutically, it's used to manage neurological and psychiatric disorders, such as depression, anxiety, and insomnia, by modulating neurotransmitter activity and neural pathways.	DUKE
Collagen-sparing		An agent that preserves collagen, reducing its degradation and promoting tissue repair. It plays a biological role in maintaining skin and joint health. Therapeutically, it has applications in wound healing, osteoarthritis, and skin rejuvenation, with key medical uses in dermatology and orthopedics to prevent tissue damage and promote regeneration.	DUKE
Cytoprotective		An agent that protects cells from damage caused by noxious chemicals, oxidative stress, or other harmful stimuli, playing a key role in preventing cell injury and death. Therapeutically, cytoprotectives are used to treat conditions such as gastroesophageal reflux disease, mucositis, and neurodegenerative disorders, with applications in oncology, gastroenterology, and neurology.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Hepatoregenerative	62868	An agent that promotes liver regeneration and repair, supporting the biological role of liver tissue restoration. It has therapeutic applications in treating liver diseases, such as cirrhosis and hepatitis, and key medical uses include enhancing liver function and reducing liver damage.	DUKE
Hepatotonic		An agent that tones and strengthens the liver, promoting liver health and function. It is used therapeutically to enhance liver regeneration, detoxification, and overall well-being, commonly used in managing liver diseases, such as hepatitis and cirrhosis, and supporting recovery from liver damage.	DUKE
Hyperemic		An agent that increases blood flow to a body part, promoting engorgement. It plays a biological role in wound healing and inflammation. Therapeutically, hyperemics are used to treat conditions like erectile dysfunction and poor circulation. Key medical uses include enhancing blood flow to targeted areas, reducing ischemia, and promoting tissue oxygenation.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Hypolipidemic		An agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health.	DUKE
Hypotriglyceridemic		An agent that lowers triglyceride levels in the blood, playing a role in lipid metabolism. Therapeutically, it helps manage hypertriglyceridemia, reducing the risk of cardiovascular disease and pancreatitis, with key medical uses in treating dyslipidemia and preventing atherosclerosis.	DUKE
Lipolytic		An agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Sweetener	50505	A substance that adds sweetness to food and beverages, often used as a sugar substitute. Its biological role is to stimulate taste receptors, while its therapeutic applications include managing calorie intake and blood sugar levels. Key medical uses include treating diabetes and obesity, as well as reducing tooth decay risk.	DUKE