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Human Metabolome Database Version 2.5

 

Showing metabocard for Chlorogenic acid (HMDB03164)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:37
Update Date 2010-07-12 16:24:33
Accession Number HMDB03164
Secondary Accession Numbers Not Available
Common Name Chlorogenic acid
Description Chlorogenic 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)
Synonyms
  1. 3-(3,4-Dihydroxycinnamoyl)quinate
  2. 3-(3,4-Dihydroxycinnamoyl)quinic acid
  3. 3-Caffeoylquinate
  4. 3-Caffeoylquinic acid
  5. 3-O-Caffeoylquinic acid
  6. Chlorogenate
  7. Chlorogenic acid
  8. Heriguard
  9. Hlorogenate
  10. Hlorogenic acid
  11. 3-trans-Caffeoylquinic acid
Chemical IUPAC Name (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexane-1-carboxylic acid
Chemical Formula C16H18O9
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Polyphenols
  • Hydroxy Acids
  • Catechols
  • Keto-Acids
Sub Class
  • Long chain dihydroxy acids
Family
  • Plant Metabolite
Species
  • secondary alcohol
  • tertiary alcohol
  • 1,2-diol
  • phenol or hydroxyhetarene
  • 1,2-diphenol
  • carboxylic acid
  • carboxylic acid ester
  • alkene
  • aromatic compound
  • alpha-hydroxyacid
Biofunction
—
Application
—
Source
  • Exogenous
Average Molecular Weight 354.309
Monoisotopic Molecular Weight 354.095093
Isomeric SMILES O[C@@H]1C[C@](O)(C[C@@H](OC(=O)C=CC2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O
Canonical SMILES OC1CC(O)(CC(OC(=O)C=CC2=CC(O)=C(O)C=C2)C1O)C(O)=O
KEGG Compound ID C00852 Link Image
BioCyc ID CAFFEOYLQUINATE Link Image
BiGG ID Not Available
Wikipedia Link Chlorogenic acid Link Image
NuGOwiki Link HMDB03164 Link Image
Metagene Link HMDB03164 Link Image
METLIN ID 3498 Link Image
PubChem Compound 1794427 Link Image
PubChem Substance 152688 Link Image
ChEBI ID 16112 Link Image
CAS Registry Number 327-97-9
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) 205 - 209 oC
Experimental Water Solubility 40 mg/mL at 25 oC [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 3.44 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 0.17 [Predicted by ALOGPS]; -0.543 [Predicted by PubChem via XLOGP]; -1.01 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Bladder —
Fibroblasts —
Concentrations (Normal)
Biofluid Blood
Value 0.040 (0.030 - 0.010) uM
Age Adult:>18 yrs old
Sex Both
Patient information After consumption of 500g of tomatoes
Comments Not Available
References
  • Bugianesi R, Salucci M, Leonardi C, Ferracane R, Catasta G, Azzini E, Maiani G: Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Eur J Nutr. 2004 Dec;43(6):360-6. Epub 2004 Apr 5. [PubMed Link Image]
Biofluid Urine
Value 0.35 +/- 0.13 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information After coffee intake
Comments Not Available
References
  • Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. [PubMed Link Image]
Biofluid Urine
Value 0.012 +/- 0.0078 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Nielsen SE, Sandstrom B: Simultaneous determination of hydroxycinnamates and catechins in human urine samples by column switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Apr 25;787(2):369-79. [PubMed Link Image]
Biofluid Urine
Value 0.0014 +/- 0.0029 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Nielsen SE, Sandstrom B: Simultaneous determination of hydroxycinnamates and catechins in human urine samples by column switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Apr 25;787(2):369-79. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  9. Stavric B, Klassen R: Dietary effects on the uptake of benzo[a]pyrene. Food Chem Toxicol. 1994 Aug;32(8):727-34. [PubMed Link Image]
  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 Link Image]
  11. Wikipedia Link Image