MiMeDB: Showing metabocard for 3-Hydroxycinnamic acid (MMDBc0030307)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:02:41 UTC

Update Date

2022-08-31 17:43:29 UTC

Metabolite ID

MMDBc0030307

Metabolite Identification

Common Name

3-Hydroxycinnamic acid

Description

3-hydroxycinnamic acid, also known as m-coumaric acid, is an aromatic acid. Research has shown that E. coli K-12 can grow with 3-hydroxycinnamic acid as the sole carbon source. (EcoCyc, PMID 6345502 )

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  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -7.042  -0.168   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                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
m-Hydroxycinnamic acid	ChEBI
trans-3-Hydroxycinnamate	ChEBI
trans-3-Hydroxycinnamic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoate	Kegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
(2E)-3-(3-Hydroxyphenyl)acrylate	Generator
(e)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
3-Coumarate	Generator
m-Hydroxycinnamate	Generator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid	Generator
m-Coumarate	Generator
3'-Hydroxycinnamate	HMDB
3'-Hydroxycinnamic acid	HMDB
3-(3-Hydroxyphenyl)-2-propenoate	HMDB
3-(3-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(3-Hydroxyphenyl)acrylate	HMDB
3-(3-Hydroxyphenyl)acrylsaeure	HMDB
3-(3-Hydroxyphenyl)prop-2-enoate	HMDB
3-(3-Hydroxyphenyl)prop-2-enoic acid	HMDB
3-Hydroxycinnamate	HMDB
3-Hydroxycinnamic acid	HMDB
m-Hydroxy-cinnamate	HMDB
m-Hydroxy-cinnamic acid	HMDB
3-Coumaric acid, (e)-isomer	MeSH, HMDB
Meta-coumaric acid	MeSH, HMDB
(E)-3-(3-Hydroxyphenyl)acrylic acid	HMDB
(E)-3-Hydroxycinnamic acid	HMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-m-Coumaric acid	HMDB
trans-m-Hydroxycinnamic acid	HMDB
trans-3-Coumarate	HMDB

Molecular Formula

C₉H₈O₃

Average Mass

164.158

Monoisotopic Mass

164.047344122

IUPAC Name

(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid

Traditional Name

m-coumaric acid

CAS Registry Number

588-30-7

SMILES

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

InChI Identifier

InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+

InChI Key

KKSDGJDHHZEWEP-SNAWJCMRSA-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
Coumaric acid or derivatives
Hydroxycinnamic acid
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

3-coumaric acid (CHEBI:32357 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.37 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 (2 TMS)	splash10-0udl-1691000000-331053d0d0b85549ac0b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udl-1691000000-331053d0d0b85549ac0b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1891000000-049e1d80dd47b23e8c28	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-2900000000-91ffd4c10eaed6a17632	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00y3-6390000000-f1a30e2fb9cd1fb11341	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03xr-0900000000-4259219e89806dfe2602	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-4900000000-2157a17ec65ead35585e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00kf-9300000000-3325dd31a734dd4659bb	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-be33d196fbb525019f07	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-d256885fb0f35d3d6680	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-be33d196fbb525019f07	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-d256885fb0f35d3d6680	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1900000000-87be0242c9f5b426f6b8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-9e4128fa078e73e71cba	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-d256885fb0f35d3d6680	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9100000000-1865c168df491277a4d3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-296d14129321002679a3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9700000000-6d29cdde66b32806de5f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-9da76da83e0462c48acf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-bf33c5b8f5901c60b332	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-2900000000-11ae76e2fe36da1dfbe6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-b6bf0b46b2fa8324cf71	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00kb-0900000000-1065251e7cf92f343533	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-004i-9000000000-0a87c81608b3fbcee7c9	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-b5ad37fb931b464df7d5	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1900000000-c66c146ee9509bf8a413	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9700000000-fcc332df0fcb818fe0e0	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-408ac0dd815354188750	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-146bae2da386ca2d4f1a	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-3900000000-235b38f342376d1c9f90	2017-06-28	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-7900000000-61ee2ad0ad164a1f7550	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

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
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006146	3-Hydroxycinnamic acid	3-Hydroxycinnamic acid	Not Available	3-Hydroxycinnamic Acid Uptake	VMH	30371894
MMDBr0006147	3-Hydroxycinnamic acid	3-Hydroxycinnamic acid	Not Available	3-Hydroxycinanmic Acid Secretion	VMH	30371894
MMDBr0008179	3-Hydroxycinnamic acid	3-Hydroxycinnamic acid	Not Available	3-hydroxycinnamic acid transport in via proton symport reversible	VMH	30371894
MMDBr0014742	3-Hydroxycinnamic acid	(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid	3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0018841	Hydrogen Ion	Water	3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase	Hydroxylation	PathBank	31602464
MMDBr0018869	Hydrogen Ion	Water	Not Available		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	33	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human supragingival plaque	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	16	Human feces; Human ; Cattle	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Plant	Oil	Olea europaea	FooDB	31437929
Plant	Fruit	Rubus idaeus	FooDB	31437929
Plant		Olea europaea	FooDB	31437929
Plant		Rubus	FooDB	31437929
Plant	Juice	Pyrus communis	FooDB	31437929
Plant	Juice	Pyrus communis	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant	Juice	Pyrus communis	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant	Juice	Pyrus communis	FooDB	31437929
Plant	Peel	Pyrus communis	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant	Peel	Pyrus communis	FooDB	31437929
Plant	Fruit	Fragaria x ananassa	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant	Juice	Pyrus communis	FooDB	31437929
Plant	Fruit	Olea europaea	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Fruit	Olea europaea	FooDB	31437929
Plant	Oil	Olea europaea	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929

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 Urine	Detected and Quantified	0.148				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified			0	3.4	uM	Adult (>18 years old)	Both	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.007	0.002			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.008	0.002			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.012	0.003			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.012	0.006			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.013	0.0065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Blood	Detected and Quantified	0.014	0.006			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.019	0.013			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Blood	Detected and Quantified	0.022	0.009			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.032	0.059			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Blood	Detected and Quantified	0.046	0.012			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.051	0.017			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.052	0.065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.078	0.085			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.092	0.092			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.17	0.15			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Feces	Detected and Quantified	0.201		0.0305	1.0843	nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	28029051
Human Urine	Detected and Quantified	0.251	0.409			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.270	0.620			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.360	0.873			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Blood	Detected and Quantified	0.881	0.878			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Feces	Detected and Quantified	2.0103	0.548			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	2.0712	0.426			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	18.808	9.712			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	11.192	7.46			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	Both	Normal	HMDB	25486321
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

HMDB0001713

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

M-coumaric_acid

METLIN ID

305

PubChem Compound

637541

PDB ID

Not Available

ChEBI ID

32357

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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 ]
Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K, Takano H, Yoshikawa T, Terao J: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2005 Feb;44(1):1-9. doi: 10.1007/s00394-004-0482-2. Epub 2004 Feb 18. [PubMed:15309457 ]
Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. doi: 10.1021/jf049560y. [PubMed:15479001 ]
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 ]
Kim MJ, Choi SJ, Kim HK, Kim CJ, Hong B, Kim YJ, Shin DH: Activation effects of Allium tuberosum Rottl. on choline acetyltransferase. Biosci Biotechnol Biochem. 2007 Jan;71(1):226-30. doi: 10.1271/bbb.60314. Epub 2007 Jan 7. [PubMed:17213651 ]
Shahidi F, Alasalvar C, Liyana-Pathirana CM: Antioxidant phytochemicals in hazelnut kernel (Corylus avellana L.) and hazelnut byproducts. J Agric Food Chem. 2007 Feb 21;55(4):1212-20. doi: 10.1021/jf062472o. Epub 2007 Jan 24. [PubMed:17249682 ]
Liu HL, Wan X, Huang XF, Kong LY: Biotransformation of sinapic acid catalyzed by Momordica charantia peroxidase. J Agric Food Chem. 2007 Feb 7;55(3):1003-8. doi: 10.1021/jf0628072. [PubMed:17263505 ]
Colen CB, Seraji-Bozorgzad N, Marples B, Galloway MP, Sloan AE, Mathupala SP: Metabolic remodeling of malignant gliomas for enhanced sensitization during radiotherapy: an in vitro study. Neurosurgery. 2006 Dec;59(6):1313-23; discussion 1323-4. doi: 10.1227/01.NEU.0000249218.65332.BF. [PubMed:17277695 ]
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Koistinen VM (2019). Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510. University of Eastern Finland.

Showing metabocard for 3-Hydroxycinnamic acid (MMDBc0030307)

MOL for #<Metabolite:0x00007f5a912c30b0>

3D MOL for #<Metabolite:0x00007f5a912c30b0>

3D SDF for #<Metabolite:0x00007f5a912c30b0>

3D-SDF for #<Metabolite:0x00007f5a912c30b0>

PDB for #<Metabolite:0x00007f5a912c30b0>

3D PDB for #<Metabolite:0x00007f5a912c30b0>

SMILES for #<Metabolite:0x00007f5a912c30b0>

INCHI for #<Metabolite:0x00007f5a912c30b0>

Structure for #<Metabolite:0x00007f5a912c30b0>

3D Structure for #<Metabolite:0x00007f5a912c30b0>