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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2020-02-26 21:24:25 UTC
HMDB IDHMDB0003164
Secondary Accession Numbers
  • HMDB03164
Metabolite Identification
Common NameChlorogenic acid
DescriptionChlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinson's disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID: 16507475 , 17368041 ).
Structure
Data?1582752265
Synonyms
ValueSource
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
Chemical FormulaC16H18O9
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
IUPAC Name(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Traditional Namechlorogenic acid
CAS Registry Number327-97-9
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
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 KeyCWVRJTMFETXNAD-JUHZACGLSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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 FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-0975000000-7ff0681e9983191145acSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846Spectrum
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-7ff0681e9983191145acSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0975000000-25fbc0fd86e2102b1846Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-1897000000-1bf40e61c8b016f6d1feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9424000000-5a5e7a151673f74acf94Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-3322039000-dccdea510eeadb723d61Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-c967ed2de6bc445ffb02Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-4fb0aa23529c84f7e829Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-029j-1900000000-7ae6eafda8c4a3c22517Spectrum
LC-MS/MSLC-MS/MS Spectrum - FD-B (Unknown) , Positivesplash10-0udi-0009000000-378f6298ca0416519525Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0009000000-0b3427977e0c1f9d6a75Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0901000000-e3869338c5312cfd01a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-4f7df62a909594e8dabfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-4438cf2b7d3dd0ca06a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-3900000000-a7982b43b83d191b2651Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-08fr-0927000000-708aeb0e652c03f8b1dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-ae6e117173e672cfa4e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-0900000000-9847301060b85490005aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-0900000000-2bcf6303448c0b3ed50aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00li-2900000000-0943d4e9b9fc1a7d947fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-6d376727bd1d633ce205Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01ot-0900000000-8515e331dca6691469afSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0900000000-21182fce172fa6b497d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-2900000000-0cab1210002740e149b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udl-0609000000-83c24cdc722253a22133Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0918000000-3ee17b66f5461b5349a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g3-0902000000-adb0080c997613268656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-837dabfad86490278224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-0519000000-d321b79970ee8839fc24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vm-1922000000-410b2ca167dfdb9d0a54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-090aec697972e64791aaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Bladder
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.040 (0.010-0.030) uMAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 467 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 467 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 467 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 467 details
UrineDetected and Quantified0.35 +/- 0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.280 +/- 0.520 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.660 +/- 0.680 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.012 +/- 0.0078 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0014 +/- 0.0029 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12029
Phenol Explorer Compound ID948
FooDB IDFDB002582
KNApSAcK IDC00002724
Chemspider ID1405788
KEGG Compound IDC00852
BioCyc IDCAFFEOYLQUINATE
BiGG IDNot Available
Wikipedia LinkChlorogenic_acid
METLIN ID3498
PubChem Compound1794427
PDB IDNot Available
ChEBI ID16112
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, Scalbert A: Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr. 2006 May;136(5):1192-7. [PubMed:16614403 ]
  2. Cremin P, Kasim-Karakas S, Waterhouse AL: LC/ES-MS detection of hydroxycinnamates in human plasma and urine. J Agric Food Chem. 2001 Apr;49(4):1747-50. [PubMed:11308321 ]
  3. Olthof MR, Hollman PC, Buijsman MN, van Amelsvoort JM, Katan MB: Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr. 2003 Jun;133(6):1806-14. [PubMed:12771321 ]
  4. Tokunaga T, Morshed SR, Otsuki S, Takayama F, Satoh T, Hashimoto K, Yasui T, Ogawa S, Kanegae H, Yokote Y, Akahane K, Kashimata M, Satoh K, Sakagami H: Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride. Anticancer Res. 2003 Sep-Oct;23(5A):3719-26. [PubMed:14666669 ]
  5. Ejzemberg R, Da Silva MH, Pinto L, Mors WB: Action of chlorogenic acid on the complement system. An Acad Bras Cienc. 1999;71(2):273-7. [PubMed:10412494 ]
  6. Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD: Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14. [PubMed:15374625 ]
  7. Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. [PubMed:11439108 ]
  8. Lafay S, Morand C, Manach C, Besson C, Scalbert A: Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Br J Nutr. 2006 Jul;96(1):39-46. [PubMed:16869989 ]
  9. Stavric B, Klassen R: Dietary effects on the uptake of benzo[a]pyrene. Food Chem Toxicol. 1994 Aug;32(8):727-34. [PubMed:8070737 ]
  10. Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
  11. Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [PubMed:16507475 ]
  12. Bonita JS, Mandarano M, Shuta D, Vinson J: Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies. Pharmacol Res. 2007 Mar;55(3):187-98. Epub 2007 Jan 26. [PubMed:17368041 ]