Human Metabolome Database Version 3.5

Showing metabocard for Caffeic acid (HMDB01964)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:29 -0600
Update Date 2013-05-29 13:32:59 -0600
HMDB ID HMDB01964
Secondary Accession Numbers None
Metabolite Identification
Common Name Caffeic acid
Description Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (PMID:16870009 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3,4-Dihydroxybenzeneacrylate
  2. 3,4-Dihydroxybenzeneacrylic acid
  3. 3,4-Dihydroxycinnamate
  4. 3,4-Dihydroxycinnamic acid
  5. Caffeate
  6. Caffeic acid pure
  7. Caffeicacid
  8. cis-Caffeate
  9. cis-Caffeic acid
Chemical Formula C9H8O4
Average Molecular Weight 180.1574
Monoisotopic Molecular Weight 180.042258744
IUPAC Name (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Name cis-caffeic acid
CAS Registry Number 331-39-5
SMILES OC(=O)\C=C/C1=CC=C(O)C(O)=C1
InChI Identifier InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-
InChI Key QAIPRVGONGVQAS-RQOWECAXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Cinnamic Acid Derivatives
Sub Class Hydroxycinnamic Acid Derivatives
Other Descriptors
  • Caffeate derivatives(KEGG)
  • Cinnamic Acid Derivatives
  • Coumaric Acid Derivatives
  • Organic Compounds
  • caffeic acid(ChEBI)
Substituents
  • 1,2 Diphenol
  • Allyl Alcohol
  • Carboxylic Acid
  • Enone
  • Phenol
  • Phenol Derivative
  • Phenylpropene
  • Styrene
Direct Parent Hydroxycinnamic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 225 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 1.15 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 1.61 g/L ALOGPS
LogP 1.67 ALOGPS
LogP 1.53 ChemAxon
LogS -2.05 ALOGPS
pKa (strongest acidic) 3.14 ChemAxon
pKa (strongest basic) -6.3 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 47.02 ChemAxon
Polarizability 17.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
  • Platelet
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.12 +/- 1.547 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
1.943 +/- 1.055 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
3.915 +/- 1.695 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.702 +/- 0.223 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.366 +/- 0.088 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.241 +/- 0.041 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.428 +/- 0.147 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
2.434 +/- 2.174 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.033 +/- 0.000 uM Adult (>18 years old) Both Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
Urine Detected and Quantified
3.5 (1.2-22.9) umol/mmol creatinine Children (1-13 year old) Both Comment Normal
Urine Detected and Quantified
2.1 (0.1-6.1) umol/mmol creatinine Children (1-13 year old) Both Comment Normal
Urine Detected and Quantified
2.6 (1.2-4.1) umol/mmol creatinine Adolescent (13-18 years old) Both Comment Normal
Urine Detected and Quantified
240 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
620 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.0065 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.019 +/-- 0.032 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.046 +/- 0.019 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.026 +/- 0.026 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.13 +/- 0.032 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.026 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.013 +/- 0.0065 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.382 +/- 0.065 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID 457 Link_out
FoodDB ID FDB002558
KNApSAcK ID Not Available
Chemspider ID 1266077 Link_out
KEGG Compound ID C01481 Link_out
BioCyc ID CAFFEATE Link_out
BiGG ID Not Available
Wikipedia Link Caffeic_acid Link_out
NuGOwiki Link HMDB01964 Link_out
Metagene Link HMDB01964 Link_out
METLIN ID 3316 Link_out
PubChem Compound 1549111 Link_out
PDB ID Not Available
ChEBI ID 17395 Link_out
References
Synthesis Reference Not 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 Link_out
  2. Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. Pubmed: 12207832 Link_out
  3. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. Pubmed: 10706426 Link_out
  4. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979 Link_out
  5. Uno J, Tanaka R, Branchini ML, Aoki FH, Yarita K, Sano A, Fukushima K, Mikami Y, Nishimura K, Miyaji M: Atypical Cryptococcus neoformans isolate from an HIV-infected patient in Brazil. Nippon Ishinkin Gakkai Zasshi. 2001;42(3):127-32. Pubmed: 11479533 Link_out
  6. Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F: In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. Int J Pharm. 2000 Apr 10;199(1):39-47. Pubmed: 10794925 Link_out
  7. Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. Pubmed: 16613584 Link_out
  8. Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. Pubmed: 15866491 Link_out
  9. 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 Link_out
  10. Olthof MR, Hollman PC, Katan MB: Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. Pubmed: 11208940 Link_out
  11. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8. Pubmed: 16870009 Link_out

Enzymes
Name: Arachidonate 5-lipoxygenase
Reactions: Not Available
Gene Name: ALOX5
Uniprot ID: P09917 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA