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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-23 06:16:16 UTC

Update Date

2023-02-21 17:31:09 UTC

HMDB ID

HMDB0062775

Secondary Accession Numbers

HMDB62775

Metabolite Identification

Common Name

4-Vinylphenol sulfate

Description

4-Vinylphenol sulfate, also known as 4-vinylphenol sulphuric acid, is a member of the class of compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. 4-Vinylphenol sulfate is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). 4-Vinylphenol sulfate can be found in blood and urine.

Structure

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

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0       0.000   4.620   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12    6                                                       
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
4-Vinylphenol sulfuric acid	Generator
4-Vinylphenol sulphate	Generator
4-Vinylphenol sulphuric acid	Generator

Chemical Formula

C₈H₈O₄S

Average Molecular Weight

200.21

Monoisotopic Molecular Weight

200.014329912

IUPAC Name

(4-ethenylphenyl)oxidanesulfonic acid

Traditional Name

(4-ethenylphenyl)oxidanesulfonic acid

CAS Registry Number

131351-90-1

SMILES

OS(=O)(=O)OC1=CC=C(C=C)C=C1

InChI Identifier

InChI=1S/C8H8O4S/c1-2-7-3-5-8(6-4-7)12-13(9,10)11/h2-6H,1H2,(H,9,10,11)

InChI Key

IETVQHUKTKKBFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

Alternative Parents

Substituents

Phenylsulfate
Phenoxy compound
Styrene
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl sulfate (CHEBI:82931 )
styrenes (CHEBI:82931 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24740205)

Excreta

Biofluid or Excreta

Urine (PMID: 27510537)

Source

Endogenous

Endogenous (HMDB: HMDB0062775)

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Lagomorph

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Poultry

Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)

Equine

Horse (FooDB: FOOD00378)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.87 g/l	ALOGPS
LogP	-0.37	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.37	ALOGPS
logP	1.93	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.72 m³·mol⁻¹	ChemAxon
Polarizability	18.38 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]+	143.896	31661259
DarkChem	[M-H]-	141.917	31661259
DeepCCS	[M+H]+	138.651	30932474
DeepCCS	[M-H]-	136.256	30932474
DeepCCS	[M-2H]-	170.94	30932474
DeepCCS	[M+Na]+	145.486	30932474
AllCCS	[M+H]+	142.6	32859911
AllCCS	[M+H-H2O]+	138.3	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.7	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	138.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.69 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4658 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1674.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	419.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	269.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	463.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	573.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	200.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1041.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	377.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1259.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	463.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	252.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	82.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Vinylphenol sulfate	OS(=O)(=O)OC1=CC=C(C=C)C=C1	2779.2	Standard polar	33892256
4-Vinylphenol sulfate	OS(=O)(=O)OC1=CC=C(C=C)C=C1	1563.3	Standard non polar	33892256
4-Vinylphenol sulfate	OS(=O)(=O)OC1=CC=C(C=C)C=C1	1727.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Vinylphenol sulfate,1TMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1739.7	Semi standard non polar	33892256
4-Vinylphenol sulfate,1TMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1720.2	Standard non polar	33892256
4-Vinylphenol sulfate,1TMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	2394.2	Standard polar	33892256
4-Vinylphenol sulfate,1TBDMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	1989.5	Semi standard non polar	33892256
4-Vinylphenol sulfate,1TBDMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	1948.9	Standard non polar	33892256
4-Vinylphenol sulfate,1TBDMS,isomer #1	C=CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2488.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Vinylphenol sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-5910000000-b7d94b4bf9b7160da275	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Vinylphenol sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 10V, Positive-QTOF	splash10-0udi-0390000000-e3214a754452b68a4db2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 20V, Positive-QTOF	splash10-0ul0-0910000000-1babafd65b899fa09738	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 40V, Positive-QTOF	splash10-0f76-9300000000-1eba3690894367e45d4e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 10V, Negative-QTOF	splash10-0002-0900000000-7cf16048a26f0fbf98ec	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 20V, Negative-QTOF	splash10-014i-0900000000-d99af63ab1f2609c4849	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 40V, Negative-QTOF	splash10-014i-6900000000-fe6f3bf7b1ed8ddb89c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 10V, Positive-QTOF	splash10-0udi-0090000000-f95c54f5ef6ceacc62d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 20V, Positive-QTOF	splash10-0udi-0910000000-4bc79eb95d0e63601d2d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 40V, Positive-QTOF	splash10-0ufr-9800000000-1ffdf2680a9adf8369fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 10V, Negative-QTOF	splash10-0002-0900000000-687669b6fe2fce4f936a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 20V, Negative-QTOF	splash10-0002-4900000000-a55e239232ff10f49cc2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylphenol sulfate 40V, Negative-QTOF	splash10-0002-9200000000-b24e7ed67fbba83f107f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB034852

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6426766

PDB ID

Not Available

ChEBI ID

82931

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:12478566 ]
Petersen AK, Zeilinger S, Kastenmuller G, Romisch-Margl W, Brugger M, Peters A, Meisinger C, Strauch K, Hengstenberg C, Pagel P, Huber F, Mohney RP, Grallert H, Illig T, Adamski J, Waldenberger M, Gieger C, Suhre K: Epigenetics meets metabolomics: an epigenome-wide association study with blood serum metabolic traits. Hum Mol Genet. 2014 Jan 15;23(2):534-45. doi: 10.1093/hmg/ddt430. Epub 2013 Sep 6. [PubMed:24014485 ]

Showing metabocard for 4-Vinylphenol sulfate (HMDB0062775)

MOL for HMDB0062775 (4-Vinylphenol sulfate)

3D MOL for HMDB0062775 (4-Vinylphenol sulfate)

3D SDF for HMDB0062775 (4-Vinylphenol sulfate)

3D-SDF for HMDB0062775 (4-Vinylphenol sulfate)

PDB for HMDB0062775 (4-Vinylphenol sulfate)

3D PDB for HMDB0062775 (4-Vinylphenol sulfate)

SMILES for HMDB0062775 (4-Vinylphenol sulfate)

INCHI for HMDB0062775 (4-Vinylphenol sulfate)

Structure for HMDB0062775 (4-Vinylphenol sulfate)

3D Structure for HMDB0062775 (4-Vinylphenol sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra