Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2018-05-29 00:35:36 UTC
Primary IDFDB002582
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChlorogenic acid
DescriptionChlorogenic acid is a hydroxycinnamic acid, a member of a family of naturally occurring organic compounds. These are esters of polyphenolic caffeic acid and cyclitol (-)-quinic acid. It is one of the phenols found in coffee, bamboo Phyllostachys edulis, as well as many other plants.
CAS Number327-97-9
Structure
Thumb
Synonyms
SynonymSource
3-(3,4-Dihydroxycinnamoyl)quinic acidChEBI
3-Caffeoylquinic acidChEBI
3-O-Caffeoylquinic acidChEBI
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acidChEBI
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidChEBI
Caffeoyl quinic acidChEBI
ChlorogenateChEBI
trans-5-O-Caffeoyl-D-quinateChEBI
3-(3,4-Dihydroxycinnamoyl)quinateGenerator
3-CaffeoylquinateGenerator
3-O-CaffeoylquinateGenerator
5-O-(3,4-Dihydroxycinnamoyl)-L-quinateGenerator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidGenerator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidGenerator
Caffeoyl quinateGenerator
trans-5-O-Caffeoyl-D-quinic acidGenerator
3-trans-Caffeoylquinic acidHMDB
HeriguardHMDB
HlorogenateHMDB
Hlorogenic acidHMDB
Acid, chlorogenicHMDB
3 Caffeoylquinic acidHMDB
Acid, 3-caffeoylquinicHMDB
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidGenerator
5-Caffeoylquinic acid?manual
5-O-Caffeoylquinic acid?manual
Caffetannic aciddb_source
Chlorogenic aciddb_source
Helianthic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility3.44 g/LALOGPS
logP0.17ALOGPS
logP-0.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.23 m³·mol⁻¹ChemAxon
Polarizability33.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H18O9
IUPAC name(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
InChI IdentifierInChI=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 KeyCWVRJTMFETXNAD-JUHZACGLSA-N
Isomeric SMILESO[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 Weight354.3087
Monoisotopic Molecular Weight354.095082174
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.24%; H 5.12%; O 40.64%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data325 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052b-0975000000-7ff0681e9983191145acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-7ff0681e9983191145acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9424000000-5a5e7a151673f74acf94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-3322039000-dccdea510eeadb723d61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-c967ed2de6bc445ffb02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-4fb0aa23529c84f7e829View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-029j-1900000000-7ae6eafda8c4a3c22517View in MoNA
LC-MS/MSLC-MS/MS Spectrum - FD-B (Unknown) , Positivesplash10-0udi-0009000000-378f6298ca0416519525View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0009000000-0b3427977e0c1f9d6a75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0901000000-e3869338c5312cfd01a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-4f7df62a909594e8dabfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-4438cf2b7d3dd0ca06a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-3900000000-a7982b43b83d191b2651View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-08fr-0927000000-708aeb0e652c03f8b1dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-ae6e117173e672cfa4e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-0900000000-9847301060b85490005aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-0900000000-2bcf6303448c0b3ed50aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00li-2900000000-0943d4e9b9fc1a7d947fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-6d376727bd1d633ce205View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ot-0900000000-8515e331dca6691469afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0900000000-21182fce172fa6b497d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-2900000000-0cab1210002740e149b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udl-0609000000-83c24cdc722253a22133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0918000000-3ee17b66f5461b5349a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g3-0902000000-adb0080c997613268656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-837dabfad86490278224View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-0519000000-d321b79970ee8839fc24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vm-1922000000-410b2ca167dfdb9d0a54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-090aec697972e64791aaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID1405788
ChEMBL IDCHEMBL284616
KEGG Compound IDC00852
Pubchem Compound ID1794427
Pubchem Substance IDNot Available
ChEBI ID16112
Phenol-Explorer ID948
DrugBank IDNot Available
HMDB IDHMDB03164
CRC / DFC (Dictionary of Food Compounds) IDCMM44-X:CMM44-X
EAFUS IDNot Available
Dr. Duke ID3-O-CAFFEOYLQUINIC-ACID|CAFFEOYL-3-QUINIC-ACID|CHLOROGENIC-ACID|CAFFETANNIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002724
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChlorogenic_acid
Phenol-Explorer Metabolite ID475
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 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
allelochemicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 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 atherosclerotic38070 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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Epstein-Barr virus22587 A substance that destroys or inhibits replication of viruses.DUKE
anti feedantDUKE
anti genotoxic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gonadotropicDUKE
anti hemolytic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypercholesterolemicDUKE
anti hyperthyroid52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti legionella33282 A substance that kills or slows the growth of bacteria.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti melanogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti nitrosaminicDUKE
antioxidant22586 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 peroxidantDUKE
anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thyroidDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
autotoxicDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardioprotective38070 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
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholagogueDUKE
cholereticDUKE
clastogenicDUKE
central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
collagen-sparingDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
histamine inhibitor37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
immunostimulant50847 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
insectifuge24852 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
interferonogenicDUKE
juvabionalDUKE
larvistatDUKE
leukotriene inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
lipoxygenase inhibitor35856 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 chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
nitric-oxide-genicDUKE
ornithine-decarboxylase inhibitor23924 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 stimulantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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.