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Record Information
Version3.6
Creation Date2006-05-22 14:17:29 UTC
Update Date2016-02-11 01:05:08 UTC
HMDB IDHMDB01964
Secondary Accession NumbersNone
Metabolite Identification
Common NameCaffeic acid
DescriptionCaffeic 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 ).
Structure
Thumb
Synonyms
ValueSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
Caffeic acidChEBI
3,4-DihydroxycinnamateGenerator
(Z)-3-(3,4-Dihydroxyphenyl)prop-2-enoateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
cis-CaffeateHMDB
cis-Caffeic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
CAS Registry Number331-39-5
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 KeyInChIKey=QAIPRVGONGVQAS-RQOWECAXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.15SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility1.61 mg/mLALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m3·mol-1ChemAxon
Polarizability17.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9341000000-6dc8d392552b88bd4d8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9351000000-50a6f144c73d7ab2794eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-2793000000-251334452407128b38bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-298c46c83441485d1d70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9800000000-942c1934d3c7c395499eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-e9bdfc2dec7a449ccb11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-b07143eccfcbf1caba0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-8f21d50b78f0d9fde98aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-4013461a961ebed6fd99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0019-2900000000-b41600c20a73cd258d40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-8900000000-81ea3878c2912bdddf71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-a1680074d0439bcd4c20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-096221135a729c5d6aacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0019-0900000000-98893b92962a162b2fb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-fc2581b0410dd8cb6e71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-9200000000-0fd7b8f57372dc8172d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-454a31169c27631fb00cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-eb2466a330b617695c80View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-3c93f113512b8284301dView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Platelet
  • Prostate
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.12 +/- 1.547 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.943 +/- 1.055 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.915 +/- 1.695 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.702 +/- 0.223 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.366 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.241 +/- 0.041 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.428 +/- 0.147 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.434 +/- 2.174 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.033 +/- 0.000 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified11.268 +/- 1.388 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.490 +/- 3.663 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.545 +/- 1.665 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.823 +/- 1.776 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified14.987 +/- 13.322 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineDetected and Quantified3.5 (1.2-22.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.1 (0.1-6.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.6 (1.2-4.1) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.16 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.41 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0065 +/- 0.013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.019 +/- 0.032 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.046 +/- 0.019 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.026 +/- 0.026 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.13 +/- 0.032 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.026 +/- 0.013 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.013 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.382 +/- 0.065 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID457
FoodDB IDFDB002558
KNApSAcK IDNot Available
Chemspider ID1266077
KEGG Compound IDC01481
BioCyc IDCAFFEATE
BiGG IDNot Available
Wikipedia LinkCaffeic_acid
NuGOwiki LinkHMDB01964
Metagene LinkHMDB01964
METLIN ID3316
PubChem Compound1549111
PDB IDNot Available
ChEBI ID17395
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [8087979 ]
  2. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [10706426 ]
  3. 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. [10794925 ]
  4. 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. [12771329 ]
  5. 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. [16614403 ]
  6. 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. [12207832 ]
  7. 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. [11479533 ]
  8. Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. [16613584 ]
  9. 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. [15866491 ]
  10. Olthof MR, Hollman PC, Katan MB: Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. [11208940 ]
  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. [16870009 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595