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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 22:05:42 UTC

Update Date

2021-09-07 16:45:35 UTC

HMDB ID

HMDB0003501

Secondary Accession Numbers

HMDB0006494
HMDB03501
HMDB06494

Metabolite Identification

Common Name

cis-Caffeic acid

Description

Caffeic acid, also known as caffeate, 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. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g).

Structure

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

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.197  -2.111   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.443  -3.016   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.197  -0.571   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2   11                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dihydroxycinnamic acid	ChEBI
Caffeate	ChEBI
Caffeic acid	ChEBI
3,4-Dihydroxycinnamate	Generator
cis-Caffeate	Generator
3,4-Dihydroxybenzeneacrylate	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
Caffeic acid pure	HMDB
Caffeicacid	HMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(Z)-Caffeic 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
Isocaffeic acid	HMDB
cis-3,4-Dihydroxycinnamic acid	HMDB
cis-Caffeic acid	HMDB

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 Name

caffeicacid

CAS Registry Number

4361-87-9

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-RQOWECAXSA-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:17395 )

Ontology

Not Available

Endogenous (HMDB: HMDB0003501)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Nut

Nuts (FooDB: FOOD00869)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.35	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	130.714	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000431

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	1.53	ChemAxon
pKa (Strongest Acidic)	3.14	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	16.85 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.558	30932474
DeepCCS	[M-H]-	137.163	30932474
DeepCCS	[M-2H]-	171.302	30932474
DeepCCS	[M+Na]+	145.782	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.2	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	135.6	32859911
AllCCS	[M+Na-2H]-	136.3	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.29 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	-2.26 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8276 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.33 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1155.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	90.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	365.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	282.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	227.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	720.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	275.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	932.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	529.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	264.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	182.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-Caffeic acid	OC(=O)\C=C/C1=CC(O)=C(O)C=C1	3629.6	Standard polar	33892256
cis-Caffeic acid	OC(=O)\C=C/C1=CC(O)=C(O)C=C1	1854.3	Standard non polar	33892256
cis-Caffeic acid	OC(=O)\C=C/C1=CC(O)=C(O)C=C1	1936.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Caffeic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O)=C1	2182.0	Semi standard non polar	33892256
cis-Caffeic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C\C(=O)O)=CC=C1O	2036.4	Semi standard non polar	33892256
cis-Caffeic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O	2059.3	Semi standard non polar	33892256
cis-Caffeic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(O)=C1	2100.4	Semi standard non polar	33892256
cis-Caffeic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O[Si](C)(C)C)=C1	2086.1	Semi standard non polar	33892256
cis-Caffeic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O[Si](C)(C)C	2090.2	Semi standard non polar	33892256
cis-Caffeic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2131.4	Semi standard non polar	33892256
cis-Caffeic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O)=C1	2426.0	Semi standard non polar	33892256
cis-Caffeic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O)=CC=C1O	2319.3	Semi standard non polar	33892256
cis-Caffeic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O	2338.2	Semi standard non polar	33892256
cis-Caffeic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2644.7	Semi standard non polar	33892256
cis-Caffeic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2606.5	Semi standard non polar	33892256
cis-Caffeic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	2647.2	Semi standard non polar	33892256
cis-Caffeic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2874.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FooDB ID

FDB012666

KNApSAcK ID

Not Available

Chemspider ID

1266077

KEGG Compound ID

C01481

BioCyc ID

CPD-8098

BiGG ID

Not Available

Wikipedia Link

Caffeic acid

METLIN ID

3316

PubChem Compound

1549111

PDB ID

Not Available

ChEBI ID

17395

Food Biomarker Ontology

Not Available

VMH ID

34DHCINM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Enzyme Details

2. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

cis-Caffeic acid → Ferulic acid	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

cis-Caffeic acid → 6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
cis-Caffeic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
cis-Caffeic acid → 6-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

4. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

cis-Caffeic acid → Caffeic acid 3-O-sulfate	details

Showing metabocard for cis-Caffeic acid (HMDB0003501)

MOL for HMDB0003501 (cis-Caffeic acid)

3D MOL for HMDB0003501 (cis-Caffeic acid)

3D SDF for HMDB0003501 (cis-Caffeic acid)

3D-SDF for HMDB0003501 (cis-Caffeic acid)

PDB for HMDB0003501 (cis-Caffeic acid)

3D PDB for HMDB0003501 (cis-Caffeic acid)

SMILES for HMDB0003501 (cis-Caffeic acid)

INCHI for HMDB0003501 (cis-Caffeic acid)

Structure for HMDB0003501 (cis-Caffeic acid)

3D Structure for HMDB0003501 (cis-Caffeic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions