MiMeDB: Showing metabocard for Caffeic acid (MMDBc0000577)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:20 UTC

Update Date

2024-10-09 22:34:05 UTC

Metabolite ID

MMDBc0000577

Metabolite Identification

Common Name

Caffeic acid

Description

Caffeic acid (CAS: 331-39-5) 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 ). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.625   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.958   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.292   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.292  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.958  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.625  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.291   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.043   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.376   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.376   3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.710   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.626   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.626  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
Caffeic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;	HMDB

Molecular Formula

C₉H₈O₄

Average Mass

180.1574

Monoisotopic Mass

180.042258744

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

caffeic acid

CAS Registry Number

Not Available

SMILES

OC(=O)\C=C\C1=CC(O)=C(O)C=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-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Epidermis
Feces
Platelet
Prostate
Urine

Tissue Locations

Epidermis
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192584	Arachidonate 5-lipoxygenase	Unknown	P09917	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012779	Caffeic acid	3-(3-Hydroxyphenyl)propanoic acid	Not Available	multistep reaction by bacteria	PMID: 15479001	15479001

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012791	Caffeic acid	3,4-Dihydroxyhydrocinnamic acid	Not Available	multistep reaction by bacteria		30409649
MMDBr0012793	3,4-Dihydroxyhydrocinnamic acid	Dihydrocaffeic acid 3-sulfate	Not Available	conjugation; phase-II biotransformation; sulfate-conjugation		Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012791	Caffeic acid	3,4-Dihydroxyhydrocinnamic acid	Not Available	multistep reaction by bacteria		30409649
MMDBr0012794	3,4-Dihydroxyhydrocinnamic acid	Dihydrocaffeic acid 3-O-glucuronide	Not Available	conjugation; phase-II biotransformation; glucuronide-conjugation		Manually annotated by MiMeDB team

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Colorectal cancer		Association	Human feces	HMDB	27275383
Colorectal cancer		Association	Human feces	HMDB	25037050
Colorectal cancer		Association	Human feces	HMDB	27015276
Antioxidant		Chemical reaction		PubMed	11768243
Anti-atherogenic		Animal_model		PubMed	16806235
Anti-inflammatory		Animal_model		PubMed	16806235
Traumatic brain injury	reduces	Animal_model	brain	PubMed	17074364
5-lipoxygenase	inhibitor	Animal_model	brain	PubMed	18482095
Traumatic brain injury	reduces	Animal_model		PubMed	18482095
Anti-inflammatory		Animal_model	skin	PubMed	22036979
Antioxidant		Animal_model	skin	PubMed	22036979
Dipeptidyl peptidase-iv	inhibits			PubMed	28230764
Glucose uptake	increases	Cell culture	3T3-L1 adipocytes	PubMed	28230764
Free radical scavenger		Chemical reaction		Pubchem	28415050

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	2	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.033				uM	Adult (>18 years old)	Both	Normal	HMDB	11308321
Human Urine	Detected and Quantified	0.16				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	0.317				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	0.41				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Blood	Detected and Quantified			0	18.887	uM	Adult (>18 years old)	Both	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.0065	0.013			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.013	0.0065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.019	0.032			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.026	0.013			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.026	0.026			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.046	0.019			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified			0.0460	1.410	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.13	0.032			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Blood	Detected and Quantified	0.241	0.041			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.366	0.088			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.382	0.065			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.428	0.147			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.620	0.240			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Blood	Detected and Quantified	0.702	0.223			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.760	0.567			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Blood	Detected and Quantified	1.943	1.055			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Feces	Detected and Quantified	11.268	1.388			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	11.490	3.663			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	11.545	1.665			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	11.823	1.776			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	14.987	13.322			nmol/g wet feces	Not Specified	Not Specified	Normal	HMDB	20669995
Human Urine	Detected and Quantified	2.1		0.1	6.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Blood	Detected and Quantified	2.12	1.547			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	2.434	2.174			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	2.6		1.2	4.1	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.5		1.2	22.9	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Blood	Detected and Quantified	3.915	1.695			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001964

DrugBank ID

DB01880

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Caffeic_acid

METLIN ID

Not Available

PubChem Compound

689043

PDB ID

Not Available

ChEBI ID

16433

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. doi: 10.1248/bpb.23.122. [PubMed:10706426 ]
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. doi: 10.1016/s0378-5173(00)00358-6. [PubMed:10794925 ]
Olthof MR, Hollman PC, Katan MB: Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. doi: 10.1093/jn/131.1.66. [PubMed:11208940 ]
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. Nihon Ishinkin Gakkai Zasshi. 2001;42(3):127-32. doi: 10.3314/jjmm.42.127. [PubMed:11479533 ]
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. doi: 10.1079/BJN2002620. [PubMed:12207832 ]
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. doi: 10.1093/jn/133.6.1853. [PubMed:12771329 ]
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. doi: 10.1016/j.jchromb.2005.03.005. Epub 2005 Apr 19. [PubMed:15866491 ]
Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. doi: 10.2174/138955706776361484. [PubMed:16613584 ]
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. doi: 10.1093/jn/136.5.1192. [PubMed:16614403 ]
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. doi: 10.1079/bjn20061808. [PubMed:16870009 ]
Kawaguchi H, Katsuyama Y, Danyao D, Kahar P, Nakamura-Tsuruta S, Teramura H, Wakai K, Yoshihara K, Minami H, Ogino C, Ohnishi Y, Kondo A: Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli. Appl Microbiol Biotechnol. 2017 Jul;101(13):5279-5290. doi: 10.1007/s00253-017-8270-0. Epub 2017 Apr 10. [PubMed:28396925 ]

Showing metabocard for Caffeic acid (MMDBc0000577)

MOL for #<Metabolite:0x00007f924157e420>

3D MOL for #<Metabolite:0x00007f924157e420>

3D SDF for #<Metabolite:0x00007f924157e420>

3D-SDF for #<Metabolite:0x00007f924157e420>

PDB for #<Metabolite:0x00007f924157e420>

3D PDB for #<Metabolite:0x00007f924157e420>

SMILES for #<Metabolite:0x00007f924157e420>

INCHI for #<Metabolite:0x00007f924157e420>

Structure for #<Metabolite:0x00007f924157e420>

3D Structure for #<Metabolite:0x00007f924157e420>