MiMeDB: Showing metabocard for 3,4-Dihydroxyhydrocinnamic acid (MMDBc0000516)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:32 UTC

Update Date

2024-09-27 20:52:23 UTC

Metabolite ID

MMDBc0000516

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

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

Molecular Formula

C₉H₁₀O₄

Average Mass

182.1733

Monoisotopic Mass

182.057908808

IUPAC Name

3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

dihydrocaffeic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-0921000000-69e0a3dba4177ea9ada1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-0921000000-69e0a3dba4177ea9ada1	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1900000000-8f0742a594d0db727f11	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00ur-8069000000-113cede8ffd5381ab0cb	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000f-0900000000-1dc54a535903f260b0b5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9100000000-74f0336af78b5918b04c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-1d433aef86dca3b39c53	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-4589cb5cf740dc1eefe5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-1900000000-bc36f01d18b6b4248472	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-6900000000-e57c83d231268edc054f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9700000000-53a68c60a48fdb8e01e6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9600000000-a48102a57ed6eae9a8bf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-4589cb5cf740dc1eefe5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-1900000000-8a038a280dd3f89e7884	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-6900000000-2b1f1c909f6abe0d4256	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9700000000-53a68c60a48fdb8e01e6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9600000000-a48102a57ed6eae9a8bf	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-2cfd60989d2ef67b4c9b	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-fbaa85a997efb64c857a	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0l4i-9700000000-f7bdc64c528a71696640	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-867d0860de62a4c828f0	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1900000000-7a274d4ecad972f6ce6f	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9700000000-110fe57d501253fffb52	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3900000000-53d05d44c9f04241cf04	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-6e00dd669916da3428f4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-7900000000-2bdbc4d0abb4a38f24a2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ri-0900000000-b16be98ef6ecf4a3e14e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ds-3900000000-d4579b1d6243d67dbb8d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uyj-9300000000-ead994336f6a97bcf6ee	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Antioxidant		Chemical reaction		PubMed	11768243
Antioxidant		Cell culture	Human erythrocytes	PubMed	11768243

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	5	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Coffee	Coffea arabica	FooDB	Not Available
Food	Red wine	Wine grape	FooDB	Not Available
Plant		Olea europaea	FooDB	PhytoHub
Plant		Vitis	FooDB	PhytoHub
Plant		Spinacia oleracea	FooDB	PhytoHub
Plant		Lactuca sativa	FooDB	PhytoHub
Plant		Citrus aurantiifolia	FooDB	PhytoHub
Plant		Beta vulgaris	FooDB	24285751
Plant		Black tea	FooDB	Not Available
Plant	Fruit	Olea europaea	FooDB	Phenol Explorer
Plant		Citrus limon	FooDB	PhytoHub
Plant	Fruit	Olea europaea	FooDB	Phenol Explorer
Plant	Plant	Beta vulgaris var. rubra	FooDB	DUKE
Plant		Brassica oleracea var. italica	FooDB	PhytoHub

Source Type	Activity	Data Source	Reference
Not Available	Antioxidant	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	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 Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	12663291
Human Urine	Detected and Quantified	0.27	0.079			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12663291
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	12663291
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	12771321
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	12771321
Human Blood	Detected and Quantified	0.066	0.04			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	17408528
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19333587
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19333587
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19460943
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19460943
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19671472
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19671472
Human Blood	Detected and Quantified	0.022	0.007			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.121	0.107			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.034	0.008			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.017	0.004			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.016	0.005			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.018	0.006			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.038	0.009			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.029	0.01			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19812218
Human Urine	Detected and Quantified	0.252	0.034			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.154	0.02			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.174	0.055			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19812218
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19879819
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	19879819
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Blood	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	20222713
Human Urine	Detected but not Quantified						NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 579	HMDB	20222713
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23269817
Human Feces	Detected and Quantified	12.516	3.348			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	19.377	13.504			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	23.604	27.94			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	27.776	41.828			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			0.044	3.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27015276
Human Urine	Detected and Quantified	0.63				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	10.117	14.922			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	15.849	5.603			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	4.853	2.891			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.861	2.937			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.946	5.086			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	9.273	5.803			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.63				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified	0.016	0.005			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.017	0.004			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.018	0.006			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.022	0.007			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.029	0.01			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.034	0.008			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.038	0.009			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified			0.0440	3.800	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.066	0.04			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	17408528
Human Blood	Detected and Quantified	0.121	0.107			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.154	0.02			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.174	0.055			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.252	0.034			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.27	0.079			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12663291
Human Feces	Detected and Quantified	12.516	3.348			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	19.377	13.504			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	23.604	27.940			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	27.776	41.828			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	6.946	5.086			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	9.273	5.803			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	15.849	5.603			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.861	2.937			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23269817
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	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

HMDB0000423

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

References

Synthesis Reference

Not Available

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. doi: 10.1021/jm00236a004. [PubMed:804550 ]
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. doi: 10.1023/a:1012741903996. [PubMed:11768243 ]
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. doi: 10.1016/j.jnutbio.2004.07.002. [PubMed:15607645 ]
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. doi: 10.1016/j.phymed.2003.11.002. [PubMed:15693705 ]
Rechner AR, Kroner C: Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb Res. 2005;116(4):327-34. doi: 10.1016/j.thromres.2005.01.002. Epub 2005 Feb 8. [PubMed:16038718 ]
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). Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510. University of Eastern Finland.

Showing metabocard for 3,4-Dihydroxyhydrocinnamic acid (MMDBc0000516)

MOL for #<Metabolite:0x00007fdb504cd118>

3D MOL for #<Metabolite:0x00007fdb504cd118>

3D SDF for #<Metabolite:0x00007fdb504cd118>

3D-SDF for #<Metabolite:0x00007fdb504cd118>

PDB for #<Metabolite:0x00007fdb504cd118>

3D PDB for #<Metabolite:0x00007fdb504cd118>

SMILES for #<Metabolite:0x00007fdb504cd118>

INCHI for #<Metabolite:0x00007fdb504cd118>

Structure for #<Metabolite:0x00007fdb504cd118>

3D Structure for #<Metabolite:0x00007fdb504cd118>