Record Information
Version1.0
Creation date2015-05-07 21:19:36 UTC
Update date2019-11-26 03:22:11 UTC
Primary IDFDB031207
Secondary Accession Numbers
  • FDB002582
Chemical Information
FooDB Nametrans-5-O-caffeoyl-D-quinate
DescriptionChlorogenic acid, also known as 3-caffeoylquinic acid or chlorogenate, belongs to quinic acids and derivatives class of compounds. Those 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 slightly soluble (in water) and a weakly acidic compound (based on its pKa). Chlorogenic acid can be found in a number of food items such as strawberry guava, natal plum, almond, and common cabbage, which makes chlorogenic acid a potential biomarker for the consumption of these food products. Chlorogenic acid can be found primarily in blood and urine, as well as in human bladder and fibroblasts tissues. Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid .
CAS Number327-97-9 202650-88-2
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
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
BioavailabilityYesChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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 DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052b-0975000000-7ff0681e9983191145acJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-7ff0681e9983191145acJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9424000000-5a5e7a151673f74acf94JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-3322039000-dccdea510eeadb723d61JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-c967ed2de6bc445ffb02JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-4fb0aa23529c84f7e829JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-029j-1900000000-7ae6eafda8c4a3c22517JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - FD-B (Unknown) , Positivesplash10-0udi-0009000000-378f6298ca0416519525JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0009000000-0b3427977e0c1f9d6a75JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0901000000-e3869338c5312cfd01a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-4f7df62a909594e8dabfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-4438cf2b7d3dd0ca06a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-3900000000-a7982b43b83d191b2651JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-08fr-0927000000-708aeb0e652c03f8b1dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-ae6e117173e672cfa4e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-0900000000-9847301060b85490005aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-0900000000-2bcf6303448c0b3ed50aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00li-2900000000-0943d4e9b9fc1a7d947fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-6d376727bd1d633ce205JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ot-0900000000-8515e331dca6691469afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0900000000-21182fce172fa6b497d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-2900000000-0cab1210002740e149b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udl-0609000000-83c24cdc722253a22133JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0918000000-3ee17b66f5461b5349a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g3-0902000000-adb0080c997613268656JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-837dabfad86490278224JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-0519000000-d321b79970ee8839fc24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vm-1922000000-410b2ca167dfdb9d0a54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-090aec697972e64791aaJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference