AFCDB: Chlorogenic acid (FDB002582)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2020-09-17 15:39:09 UTC

Primary ID

FDB002582

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chlorogenic acid

Description

Chlorogenic acid, also known as chlorogenate or 3-caffeoylquinate, 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. Chlorogenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chlorogenic acid has been detected, but not quantified in, several different foods, such as limes, cocoa beans, celery leaves, caraway, and epazotes. This could make chlorogenic acid a potential biomarker for the consumption of these foods.

CAS Number

327-97-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H18O9

IUPAC name

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

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

Isomeric SMILES

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

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:16112 )
tannin (CHEBI:16112 )
Caffeate derivatives (C00852 )

Ontology

Foods

Fruits and vegetables:

Beverages:

Coffee products

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 54.24%; H 5.12%; O 40.64%	DFC
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	325 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-7ff0681e9983191145ac	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-25fbc0fd86e2102b1846	Spectrum
GC-MS	Chlorogenic acid, 6 TMS, GC-MS Spectrum	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-7ff0681e9983191145ac	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-052b-0975000000-25fbc0fd86e2102b1846	Spectrum
GC-MS	Chlorogenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	Spectrum
Predicted GC-MS	Chlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-9424000000-5a5e7a151673f74acf94	Spectrum
Predicted GC-MS	Chlorogenic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-3322039000-dccdea510eeadb723d61	Spectrum
Predicted GC-MS	Chlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-c967ed2de6bc445ffb02	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0900000000-4fb0aa23529c84f7e829	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-029j-1900000000-7ae6eafda8c4a3c22517	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - FD-B (Unknown) , Positive	splash10-0udi-0009000000-378f6298ca0416519525	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0009000000-0b3427977e0c1f9d6a75	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0901000000-e3869338c5312cfd01a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-0900000000-4f7df62a909594e8dabf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-0900000000-4438cf2b7d3dd0ca06a4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-000f-3900000000-a7982b43b83d191b2651	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-08fr-0927000000-708aeb0e652c03f8b1db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0900000000-ae6e117173e672cfa4e8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03di-0900000000-9847301060b85490005a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-0900000000-2bcf6303448c0b3ed50a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00li-2900000000-0943d4e9b9fc1a7d947f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-6d376727bd1d633ce205	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-01ot-0900000000-8515e331dca6691469af	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-000i-0900000000-21182fce172fa6b497d0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-2900000000-0cab1210002740e149b4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udl-0609000000-83c24cdc722253a22133	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0918000000-3ee17b66f5461b5349a2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g3-0902000000-adb0080c997613268656	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-837dabfad86490278224	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfu-0519000000-d321b79970ee8839fc24	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vm-1922000000-410b2ca167dfdb9d0a54	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0900000000-090aec697972e64791aa	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16112

Phenol-Explorer ID

948

DrugBank ID

Not Available

HMDB ID

HMDB03164

CRC / DFC (Dictionary of Food Compounds) ID

CMM44-X:CMM44-X

EAFUS ID

Not Available

Dr. Duke ID

3-O-CAFFEOYLQUINIC-ACID|CAFFEOYL-3-QUINIC-ACID|CHLOROGENIC-ACID|CAFFETANNIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002724

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

Chlorogenic_acid

Phenol-Explorer Metabolite ID

475

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
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
allelochemic			DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti Epstein-Barr virus	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti feedant			DUKE
anti genotoxic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gonadotropic			DUKE
anti hemolytic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti hypercholesterolemic			DUKE
anti hyperthyroid	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti legionella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti leukotriene	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti melanogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti mutagenic			DUKE
anti nitrosaminic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti peroxidant			DUKE
anti polio	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti radicular			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti sunburn	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti thyroid			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
autotoxic			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardioprotective	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cholagogue			DUKE
choleretic			DUKE
clastogenic			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
central nervous system stimulant	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
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
histamine inhibitor	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
interferonogenic			DUKE
juvabional			DUKE
larvistat			DUKE
leukotriene inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
lipoxygenase inhibitor	35856	A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.	DUKE
metal chelator	38161	A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.	DUKE
nitric-oxide-genic			DUKE
ornithine-decarboxylase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
oviposition stimulant			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
sunscreen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE
vulnerary	73336	A drug used in treating and healing of wounds.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Chlorogenic acid (FDB002582)

Structure for FDB002582 (Chlorogenic acid)