MiMeDB: Showing metabocard for (E)-4-coumarate (MMDBc0054083)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:57 UTC

Update Date

2022-09-01 02:27:06 UTC

Metabolite ID

MMDBc0054083

Metabolite Identification

Common Name

(E)-4-coumarate

Description

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
(2E)-3-(4-Hydroxyphenyl)acrylate	ChEBI
trans-p-Coumarate	ChEBI
(2E)-3-(4-Hydroxyphenyl)acrylic acid	Generator
trans-p-Coumaric acid	Generator
trans-4-Coumaric acid	Generator
P-Coumaric acid	Generator

Molecular Formula

C₉H₇O₃

Average Mass

163.1501

Monoisotopic Mass

163.03951909

IUPAC Name

(2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

p-coumarate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C([O-])=O)C=C1

InChI Identifier

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/p-1/b6-3+

InChI Key

NGSWKAQJJWESNS-ZZXKWVIFSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Styrene
Phenoxide
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

4-coumarate (CHEBI:12876 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.13 g/L	ALOGPS
logP	1.77	ALOGPS
logP	1.83	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.88 m³·mol⁻¹	ChemAxon
Polarizability	15.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-85aee640bd61011bfa0b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-0900000000-adfca6ff87d8855467cd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rb-7900000000-53b5efa3ec5cbb2ddfec	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-5db2acbadef91e2aac04	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1900000000-849656d4441bcfed2584	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-1f7f93e9361768feb925	2016-09-12	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013905	(E)-4-coumarate	(E)-4-coumaroyl-CoA	4-coumarate--CoA ligase	Ligation	RHEA	34755880
MMDBr0015212	(E)-4-coumarate	4-Vinylphenol	Ferulic acid decarboxylase 1	Decarboxylation	RHEA	34755880
MMDBr0017038	Hydrogen Ion	(E)-4-coumarate	3-(aryl)acrylate reductase	Reduction	RHEA	34755880
MMDBr0017039	(E)-4-coumarate	Hydrogen Ion	3-(aryl)acrylate reductase	Reduction	RHEA	34755880
MMDBr0017918	L-Tyrosine	(E)-4-coumarate	Phenylalanine/tyrosine ammonia-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0038857	(E)-4-coumaroyl-CoA	(E)-4-coumarate	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	7
Eukaryota/Fungi	Ascomycota	3
Bacteria	Firmicutes	2	Human feces
Eukaryota/Fungi	Basidiomycota	1
Bacteria	Actinobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

COUMARATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5288519

PDB ID

Not Available

ChEBI ID

12876

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (E)-4-coumarate (MMDBc0054083)

MOL for #<Metabolite:0x00007fe26cc79790>

3D MOL for #<Metabolite:0x00007fe26cc79790>

3D SDF for #<Metabolite:0x00007fe26cc79790>

3D-SDF for #<Metabolite:0x00007fe26cc79790>

PDB for #<Metabolite:0x00007fe26cc79790>

3D PDB for #<Metabolite:0x00007fe26cc79790>

SMILES for #<Metabolite:0x00007fe26cc79790>

INCHI for #<Metabolite:0x00007fe26cc79790>

Structure for #<Metabolite:0x00007fe26cc79790>

3D Structure for #<Metabolite:0x00007fe26cc79790>