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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:49 UTC

HMDB ID

HMDB0000423

Secondary Accession Numbers

HMDB00423

Metabolite Identification

Common Name

3,4-Dihydroxyhydrocinnamic acid

Description

3,4-Dihydroxyhydrocinnamic acid, also known as dihydrocaffeic acid (DHCA), is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID: 15607645 ) and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract (PMID: 15693705 ). Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans (PMID: 16038718 ). Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243 ). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285 ).

Structure

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

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.042  -0.168   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   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 NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,4-Dihydroxy-beta-phenylpropionic acid	ChEBI
3,4-Dihydroxybenzenepropionic acid	ChEBI
3,4-Dihydroxydihydrocinnamic acid	ChEBI
3,4-Dihydroxyphenylpropionic acid	ChEBI
3-(3,4-Dihydroxyphenyl)propanoate	Kegg
3,4-Dihydroxy-b-phenylpropionate	Generator
3,4-Dihydroxy-b-phenylpropionic acid	Generator
3,4-Dihydroxy-beta-phenylpropionate	Generator
3,4-Dihydroxy-β-phenylpropionate	Generator
3,4-Dihydroxy-β-phenylpropionic acid	Generator
3,4-Dihydroxybenzenepropanoate	Generator
3,4-Dihydroxybenzenepropionate	Generator
3,4-Dihydroxydihydrocinnamate	Generator
3,4-Dihydroxyphenylpropionate	Generator
3-(3,4-Dihydroxyphenyl)propionate	Generator
Dihydrocaffeate	Generator
Hydrocaffeate	Generator
3-(3,4-Dihydroxyphenyl)propanoic acid	Generator
3,4-Dihydroxyhydrocinnamate	Generator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamate	HMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acid	HMDB
3,4-Dihydroxyphenylpropionic acid, potassium salt	HMDB
DHC	HMDB
3,4-Dihydroxyhydrocinnamic acid	HMDB
3-(3',4'-Dihydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

dihydrocaffeic acid

CAS Registry Number

1078-61-1

SMILES

OC(=O)CCC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

InChI Key

DZAUWHJDUNRCTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Catechol
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
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:48400 )
catechols (CHEBI:48400 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000423)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000423)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000423)
Urine (HMDB: HMDB0000423)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000423)

Source

Exogenous

Food

Food (HMDB: HMDB0000423)
Legumes (HMDB: HMDB0000423)

Cereal and cereal product

Leavened bread

Wheat bread (FooDB: FOOD00808)

Cereal product

Whole grain cereal products (HMDB: HMDB0000423)

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)

Vegetables (HMDB: HMDB0000423)

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000423)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000423)

Coffee

Tea

Tea products (HMDB: HMDB0000423)

Fat and oil

Olive oil (HMDB: HMDB0000423)

Fruit

Fruits (HMDB: HMDB0000423)

Berry

Grape (FooDB: FOOD00369)

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)

Nut

Nuts (HMDB: HMDB0000423)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000423)

Fermented beverage

Apple cider (FooDB: FOOD00615)

Endogenous

Plant

Plant (HMDB: HMDB0000423)

Microbe

Microbe (HMDB: HMDB0000423)
Escherichia coli (HMDB: HMDB0000423)
Clostridium (HMDB: HMDB0000423)
Bifidobacterium lactis (HMDB: HMDB0000423)
Lactobacillus gasseri (HMDB: HMDB0000423)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000423)
Antioxidant (HMDB: HMDB0000423)

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00029981)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	136 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	428 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	133.047	30932474
[M-H]-	Not Available	133.047	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000427

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.84	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	3	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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
DarkChem	[M+H]+	143.363	31661259
DarkChem	[M-H]-	137.344	31661259
AllCCS	[M+H]+	139.607	32859911
AllCCS	[M-H]-	137.876	32859911
DeepCCS	[M+H]+	138.005	30932474
DeepCCS	[M-H]-	135.192	30932474
DeepCCS	[M-2H]-	171.437	30932474
DeepCCS	[M+Na]+	146.96	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.4	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxyhydrocinnamic acid	OC(=O)CCC1=CC(O)=C(O)C=C1	3378.5	Standard polar	33892256
3,4-Dihydroxyhydrocinnamic acid	OC(=O)CCC1=CC(O)=C(O)C=C1	1819.1	Standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid	OC(=O)CCC1=CC(O)=C(O)C=C1	1814.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxyhydrocinnamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O)=C1	1974.0	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(CCC(=O)O)=CC=C1O	1933.7	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C1O	1938.7	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C(O)=C1	1901.5	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O[Si](C)(C)C)=C1	1894.8	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C1O[Si](C)(C)C	1945.1	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1956.5	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O)=C1	2199.0	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCC(=O)O)=CC=C1O	2183.3	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C1O	2180.1	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2408.3	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2379.5	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C1O[Si](C)(C)C(C)(C)C	2431.6	Semi standard non polar	33892256
3,4-Dihydroxyhydrocinnamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2631.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (3 TMS)	splash10-004i-0921000000-69e0a3dba4177ea9ada1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (Non-derivatized)	splash10-004i-0921000000-69e0a3dba4177ea9ada1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1900000000-8f0742a594d0db727f11	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00ur-8069000000-113cede8ffd5381ab0cb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000f-0900000000-1dc54a535903f260b0b5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kf-9100000000-74f0336af78b5918b04c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9000000000-1d433aef86dca3b39c53	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-001i-0900000000-4589cb5cf740dc1eefe5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-000i-1900000000-bc36f01d18b6b4248472	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0a4i-6900000000-e57c83d231268edc054f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4i-9700000000-53a68c60a48fdb8e01e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4l-9600000000-a48102a57ed6eae9a8bf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-4589cb5cf740dc1eefe5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ , negative-QTOF	splash10-000i-1900000000-8a038a280dd3f89e7884	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-6900000000-2b1f1c909f6abe0d4256	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9700000000-53a68c60a48fdb8e01e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid LC-ESI-QQ , negative-QTOF	splash10-0a4l-9600000000-a48102a57ed6eae9a8bf	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 10V, Positive-QTOF	splash10-014i-0900000000-2cfd60989d2ef67b4c9b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 20V, Positive-QTOF	splash10-00kr-0900000000-fbaa85a997efb64c857a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 40V, Positive-QTOF	splash10-0l4i-9700000000-f7bdc64c528a71696640	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 10V, Negative-QTOF	splash10-001i-0900000000-867d0860de62a4c828f0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 20V, Negative-QTOF	splash10-01qi-1900000000-7a274d4ecad972f6ce6f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 40V, Negative-QTOF	splash10-0a4l-9700000000-110fe57d501253fffb52	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 10V, Negative-QTOF	splash10-001i-3900000000-53d05d44c9f04241cf04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 20V, Negative-QTOF	splash10-000i-2900000000-6e00dd669916da3428f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 40V, Negative-QTOF	splash10-052o-7900000000-2bdbc4d0abb4a38f24a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 10V, Positive-QTOF	splash10-00ri-0900000000-b16be98ef6ecf4a3e14e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 20V, Positive-QTOF	splash10-00ds-3900000000-d4579b1d6243d67dbb8d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyhydrocinnamic acid 40V, Positive-QTOF	splash10-0uyj-9300000000-ead994336f6a97bcf6ee	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.029 +/- 0.01 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.017 +/- 0.004 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.038 +/- 0.009 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.034 +/- 0.008 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.016 +/- 0.005 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.022 +/- 0.007 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.018 +/- 0.006 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.121 +/- 0.107 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	12771321	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19671472	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19333587	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	20222713	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	12663291	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19812218	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19460943	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19879819	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.066 +/- 0.04 uM	Adult (>18 years old)	Not Specified	Normal	17408528	details
Feces	Detected and Quantified	27.776 +/- 41.828 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	12.516 +/- 3.348 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	19.377 +/- 13.504 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	23.604 +/- 27.940 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23269817	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	15.849 +/- 5.603 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	6.861 +/- 2.937 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.27 +/- 0.079 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12663291	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19671472	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19333587	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	20222713	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	12663291	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19812218	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19460943	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 579	19879819	details
Urine	Detected and Quantified	0.63 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0440-3.800 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.174 +/- 0.055 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected and Quantified	0.252 +/- 0.034 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected and Quantified	0.154 +/- 0.02 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Urine	Detected and Quantified	9.273 +/- 5.803 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	4.853 +/- 2.891 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	6.946 +/- 5.086 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	10.117 +/- 14.922 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5412

PubChem Compound

348154

PDB ID

Not Available

ChEBI ID

48400

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029981

Good Scents ID

Not Available

References

Synthesis Reference

Sabally Kebba; Karboune Salwa; St-Louis Richard; Kermasha Selim Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. Journal of biotechnology (2006), 127(1), 167-76.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [PubMed:804550 ]
Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
Huang J, de Paulis T, May JM: Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. J Nutr Biochem. 2004 Dec;15(12):722-9. [PubMed:15607645 ]
Rechner AR, Kroner C: Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb Res. 2005;116(4):327-34. Epub 2005 Feb 8. [PubMed:16038718 ]
Lekse JM, Xia L, Stark J, Morrow JD, May JM: Plant catechols prevent lipid peroxidation in human plasma and erythrocytes. Mol Cell Biochem. 2001 Oct;226(1-2):89-95. [PubMed:11768243 ]
Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. 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

3,4-Dihydroxyhydrocinnamic acid → Dihydroferulic acid	details

Enzyme Details

2. 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

3,4-Dihydroxyhydrocinnamic acid → 6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3,4-Dihydroxyhydrocinnamic acid → 6-[4-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3,4-Dihydroxyhydrocinnamic acid → 6-{[3-(3,4-dihydroxyphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. 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

3,4-Dihydroxyhydrocinnamic acid → Dihydrocaffeic acid 3-sulfate	details

Showing metabocard for 3,4-Dihydroxyhydrocinnamic acid (HMDB0000423)

MOL for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

3D MOL for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

3D SDF for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

3D-SDF for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

PDB for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

3D PDB for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

SMILES for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

INCHI for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

Structure for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

3D Structure for HMDB0000423 (3,4-Dihydroxyhydrocinnamic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions