MiMeDB: Showing metabocard for 4-Vinylphenol (MMDBc0033587)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:43 UTC

Update Date

2024-09-28 04:15:06 UTC

Metabolite ID

MMDBc0033587

Metabolite Identification

Common Name

4-Vinylphenol

Description

4-Vinylphenol is a vinylphenol, a type of pyranoanthocyanin. 4-Vinylphenol is produced by decarboxylation by phenyl acrylic acid decarboxylase of the grape compound p-coumaric acid by certain strains of S. cerevisiae. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. 4-Vinylphenol is responsible for a hospital or plaster smell. [PMID: 17303275 ]

Structure

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

Synonyms

Value	Source
4-Vinylphenol	ChEBI
p-Hydroxystyrene	ChEBI
p-Vinylphenol	ChEBI

Molecular Formula

C₈H₈O

Average Mass

120.1485

Monoisotopic Mass

120.057514878

IUPAC Name

4-ethenylphenol

Traditional Name

4-vinylphenol

CAS Registry Number

2628-17-3

SMILES

OC1=CC=C(C=C)C=C1

InChI Identifier

InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2

InChI Key

FUGYGGDSWSUORM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:1883 )
a small molecule (CPD-1075 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.4 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.41	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.73 m³·mol⁻¹	ChemAxon
Polarizability	13.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-78e97f8689a1bddce8d1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004l-1900000000-aabb90db206495e1949c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-78e97f8689a1bddce8d1	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004l-1900000000-aabb90db206495e1949c	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-e4b2ae72210dba8376c5	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-8900000000-96525d05990bd44a73e6	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 - LC-ESI-QFT , negative	splash10-014i-0900000000-4748791daa3cc6db33cb	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-b529604eb0086ce7d85a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-cc4e2accb5dbfca1223a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9300000000-1a680f497983265f7000	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-992515c0effcfff51739	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-adf06e57ffef41aa20d0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-9600000000-7855fd6420cc0a980f56	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c381eb3871f5dbd6a94	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-9800000000-e2093cd31e1a5d12f825	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-9000000000-dd7dfadb6034e83a56c0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-972f865a96261dcb891a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-cc2986e6d45482e40a36	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i2d-9000000000-6a5b5c88ab894e1f7233	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Membrane

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
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
MMDBr0012762	Luteolin	4-Hydroxycinnamic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012805	4-Vinylphenol	4-Ethylphenol	Not Available	vinyl phenol reductase

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012763	Apigenin	4-Hydroxycinnamic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012805	4-Vinylphenol	4-Ethylphenol	Not Available	vinyl phenol reductase

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012770	Hydroxyphenyllactic acid	4-Hydroxycinnamic acid	Not Available			19961416
MMDBr0012805	4-Vinylphenol	4-Ethylphenol	Not Available	vinyl phenol reductase

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	Microbial Links
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	1	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit juice	Vaccinium myrtillus	FooDB	31437929

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0004072

DrugBank ID

Not Available

Phenol Explorer Compound ID

706

FooDB ID

FDB010540

KNApSAcK ID

Not Available

Chemspider ID

56234

KEGG Compound ID

C05627

BioCyc ID

CPD-1075

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7012

PubChem Compound

62453

PDB ID

Not Available

ChEBI ID

1883

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sjoborg S, Fregert S, Trulsson L: Contact allergy to styrene and related chemicals. Contact Dermatitis. 1984 Feb;10(2):94-6. doi: 10.1111/j.1600-0536.1984.tb00342.x. [PubMed:6713846 ]
Manini P, De Palma G, Mozzoni P, Andreoli R, Poli D, Bergamaschi E, Franchini I, Mutti A: GSTM1 polymorphism and styrene metabolism: insights from an acute accidental exposure. Toxicol Lett. 2002 Aug 5;134(1-3):201-8. doi: 10.1016/s0378-4274(02)00190-x. [PubMed:12191879 ]
Manini P, Andreoli R, Poli D, De Palma G, Mutti A, Niessen WM: Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. Rapid Commun Mass Spectrom. 2002;16(24):2239-48. doi: 10.1002/rcm.848. [PubMed:12478566 ]

Showing metabocard for 4-Vinylphenol (MMDBc0033587)

MOL for #<Metabolite:0x00007f47059a98d8>

3D MOL for #<Metabolite:0x00007f47059a98d8>

3D SDF for #<Metabolite:0x00007f47059a98d8>

3D-SDF for #<Metabolite:0x00007f47059a98d8>

PDB for #<Metabolite:0x00007f47059a98d8>

3D PDB for #<Metabolite:0x00007f47059a98d8>

SMILES for #<Metabolite:0x00007f47059a98d8>

INCHI for #<Metabolite:0x00007f47059a98d8>

Structure for #<Metabolite:0x00007f47059a98d8>

3D Structure for #<Metabolite:0x00007f47059a98d8>