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Human Metabolome Database Version 3.5

Showing metabocard for Caffeic acid (HMDB01964)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (1)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2006-05-22 08:17:29 -0600
Update Date	2013-02-08 17:11:06 -0700
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 ).
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	3,4-Dihydroxybenzeneacrylate 3,4-Dihydroxybenzeneacrylic acid 3,4-Dihydroxycinnamate 3,4-Dihydroxycinnamic acid Caffeate Caffeic acid pure Caffeicacid cis-Caffeate 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 Comments Blood Detected and Quantified 2.12 +/- 1.547 uM Adult (>18 years old) Male Normal Before ingestion of water Blood Detected and Quantified 1.943 +/- 1.055 uM Adult (>18 years old) Male Normal 2 h after ingestion of water Blood Detected and Quantified 3.915 +/- 1.695 uM Adult (>18 years old) Male Normal Before ingestion of quercetin Blood Detected and Quantified 0.702 +/- 0.223 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of quercetin Blood Detected and Quantified 0.366 +/- 0.088 uM Adult (>18 years old) Male Normal Before ingestion of (-)-epicathechin Blood Detected and Quantified 0.241 +/- 0.041 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of (-)-epicathechin Blood Detected and Quantified 0.428 +/- 0.147 uM Adult (>18 years old) Male Normal Before ingestion of epigallocatechin gallate Blood Detected and Quantified 2.434 +/- 2.174 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of... Blood Detected and Quantified 0.033 +/- 0.000 uM Adult (>18 years old) Both Normal Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 457 Not Available Urine Detected and Quantified 3.5 (1.2-22.9) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 2-6 years Urine Detected and Quantified 2.1 (0.1-6.1) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 6-10 years Urine Detected and Quantified 2.6 (1.2-4.1) umol/mmol creatinine Adolescent (13-18 years old) Both Normal Children >10 years old Urine Detected and Quantified 240 umol/mmol creatinine Adult (>18 years old) Both Normal 24 hours after the 2-day diet started Urine Detected and Quantified 620 umol/mmol creatinine Adult (>18 years old) Both Normal After 2-day diet protocol Urine Detected and Quantified 0.0065 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.019 +/-- 0.032 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.046 +/- 0.019 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.026 +/- 0.026 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.13 +/- 0.032 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.026 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.013 +/- 0.0065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.382 +/- 0.065 umol/mmol creatinine Adult (>18 years old) Male Normal 5-h after ingestion of 200 mg of quercetin,...
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
Phenol Explorer Compound ID	Not Available
Phenol Explorer Metabolite ID	457
FoodDB ID	FDB002558
KNApSAcK ID	Not Available
Chemspider ID	1266077
KEGG Compound ID	C01481
BioCyc ID	CAFFEATE
BiGG ID	Not Available
Wikipedia Link	Caffeic_acid
NuGOwiki Link	HMDB01964
Metagene Link	HMDB01964
METLIN ID	3316
PubChem Compound	1549111
PDB ID	Not Available
ChEBI ID	17395
References
Synthesis Reference	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
General References	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 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 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 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 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 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 Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. Pubmed: 16613584 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 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 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 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

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Enzymes

Name: Arachidonate 5-lipoxygenase Reactions: (1) arachidonate + O2 = (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O (overall reaction) [RN:R08527] (2) (1a) arachidonate + O2 = (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate [RN:R01595] (3) (1b) (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate = (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O [RN:R03058] Gene Name: ALOX5 Uniprot ID: P09917 Protein Sequence: FASTA Gene Sequence: FASTA

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