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Showing metabocard for 4-Hydroxystyrene (HMDB0004072)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:18:14 UTC
Update Date2023-02-21 17:16:53 UTC
HMDB IDHMDB0004072
Secondary Accession Numbers
  • HMDB04072
Metabolite Identification
Common Name4-Hydroxystyrene
Description4-Hydroxystyrene, also known as 4-vinylphenol, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 4-Hydroxystyrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxystyrene exists in all eukaryotes, ranging from yeast to humans. 4-Hydroxystyrene is a sweet, almond shell, and chemical tasting compound. Outside of the human body, 4-Hydroxystyrene is found, on average, in the highest concentration within a few different foods, such as white wines, beers, and corns and in a lower concentration in taco, bilberries, and tortilla. 4-Hydroxystyrene has also been detected, but not quantified in, several different foods, such as asparagus, cauliflowers, evergreen blackberries, tea, and tortilla chips. This could make 4-hydroxystyrene a potential biomarker for the consumption of these foods. Styrene is a prohapten metabolized in the skin by aryl hydrocarbon hydroxylase (AHH, EC1.14.14.1) to styrene epoxide acting as the true hapten. Styrene occurs in nature and as a synthetic product. 4-hydroxystyrene occurs frequently in different ciders, wines, foods and berries, e.g. cloudberry.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004072 (4-Hydroxystyrene)

  Mrv1652304272018562D          

  9  9  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for HMDB0004072 (4-Hydroxystyrene)

HMDB0004072
     RDKit          3D
4-Hydroxystyrene
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.9765   -0.6245    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.3610    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.2219    0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.3299    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797    1.2291   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0496    0.0408   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -0.0392   -0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273   -1.0605   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -0.9608   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800   -1.6137    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050   -0.4410    0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870    1.3502    0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049    2.2600    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    2.0866   -0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -0.2646   -0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -2.0171   -0.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536   -1.8581   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0004072 (4-Hydroxystyrene)

  Mrv1652304272018562D          

  9  9  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004072

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.150650686578334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-ethenylphenol

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.4063825623333335

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.564744411272942

> <JCHEM_PKA_STRONGEST_BASIC>
-5.945492538502283

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
37.7252

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-vinylphenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0004072 (4-Hydroxystyrene)

HMDB0004072
     RDKit          3D
4-Hydroxystyrene
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.9765   -0.6245    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.3610    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.2219    0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.3299    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797    1.2291   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0496    0.0408   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -0.0392   -0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273   -1.0605   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -0.9608   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800   -1.6137    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050   -0.4410    0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870    1.3502    0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049    2.2600    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    2.0866   -0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -0.2646   -0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -2.0171   -0.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536   -1.8581   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0004072 (4-Hydroxystyrene)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    7                                                       
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    2    3    4                                                  
CONECT    8    5    6    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0004072 (4-Hydroxystyrene)

COMPND    HMDB0004072
HETATM    1  C1  UNL     1       2.977  -0.625   0.437  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.124   0.361   0.484  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.711   0.222   0.150  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.143   1.330   0.225  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.480   1.229  -0.084  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.050   0.041  -0.483  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.410  -0.039  -0.792  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.227  -1.060  -0.563  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.134  -0.961  -0.249  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.680  -1.614   0.143  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.005  -0.441   0.699  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.487   1.350   0.792  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.305   2.260   0.538  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.137   2.087  -0.025  1.00  0.00           H  
HETATM   15  H6  UNL     1      -4.112  -0.265  -0.075  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.617  -2.017  -0.870  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.754  -1.858  -0.326  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4    9
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7    8
CONECT    7   15
CONECT    8    9    9   16
CONECT    9   17
END
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SMILES for HMDB0004072 (4-Hydroxystyrene)

OC1=CC=C(C=C)C=C1
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INCHI for HMDB0004072 (4-Hydroxystyrene)

InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-VinylphenolChEBI
p-HydroxystyreneChEBI
p-VinylphenolChEBI
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name4-ethenylphenol
Traditional Name4-vinylphenol
CAS Registry Number2628-17-3
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 KeyFUGYGGDSWSUORM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point73.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID706
FooDB IDFDB010540
KNApSAcK IDNot Available
Chemspider ID56234
KEGG Compound IDC05627
BioCyc IDCPD-1075
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7012
PubChem Compound62453
PDB IDNot Available
ChEBI ID1883
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceShuey, Steven W. Processes for conversion of tyrosine to p-hydroxystyrene and p-acetoxystyrene. PCT Int. Appl. (2007), 28 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:12191879 ]
  2. 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 ]
  3. Sjoborg S, Fregert S, Trulsson L: Contact allergy to styrene and related chemicals. Contact Dermatitis. 1984 Feb;10(2):94-6. [PubMed:6713846 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxystyrene → 6-(4-ethenylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxystyrene → 4-Vinylphenol sulfatedetails