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Showing metabocard for Styrene (HMDB0034240)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 19:02:38 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034240
Secondary Accession Numbers
  • HMDB34240
Metabolite Identification
Common NameStyrene
DescriptionStyrene, also known as vinylbenzene or phenylethylene, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. The metabolites of styrene are excreted mainly in the urine. Styrene is possibly neutral. Styrene is a sweet, balsamic, and floral tasting compound. Styrene has been detected, but not quantified, in several different foods, such as coffee and coffee products, fruits, cocoa and cocoa products, alcoholic beverages, and chinese cinnamons. This could make styrene a potential biomarker for the consumption of these foods. A minor pathway of styrene metabolism involves the formation of phenylacetaldehyde from styrene 7,8-oxide or cytochrome P450 conversion of styrene to pheylethanol and subsequent metabolism to phenylacetic acid. Styrene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Styrene oxide is predominantly metabolized by epoxide hydrolase to form styrene glycol; the styrene glycol is subsequently converted to mandelic acid, phenylglyoxylic acid, and hippuric acid. Styrene, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease and ulcerative colitis; styrene has also been linked to the inborn metabolic disorder celiac disease. Styrene may be absorbed following ingestion, inhalation, or dermal exposure. Breathing high levels of styrene may cause nervous system effects such as changes in color vision, tiredness, feeling drunk, slowed reaction time, concentration problems, or balance problems. Chest burning, wheezing, and dyspnea may also occur. Styrene causes nervous system depression and may be carcinogenic.
Structure
Data?1601267889
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034240 (Styrene)

  Mrv1652309272007432D          

  8  8  0  0  0  0            999 V2000
    0.5802    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0034240 (Styrene)

HMDB0034240
     RDKit          3D
Styrene
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.6741   -0.0525    0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8759    0.4731   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    0.1899   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899   -0.6480    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -0.8836    0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.2901   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6884    0.5505   -1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    0.7860   -1.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -0.7256    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.1573    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.1448   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612   -1.1538    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -1.5534    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983   -0.4846   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    1.0388   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613    1.4512   -1.7928 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
  7  8  2  0
  8  3  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0034240 (Styrene)

  Mrv1652309272007432D          

  8  8  0  0  0  0            999 V2000
    0.5802    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034240

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2

> <INCHI_KEY>
PPBRXRYQALVLMV-UHFFFAOYSA-N

> <FORMULA>
C8H8

> <MOLECULAR_WEIGHT>
104.1491

> <EXACT_MASS>
104.062600256

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.176898359735938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethenylbenzene

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.709947884

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
35.744299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
styrene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034240 (Styrene)

HMDB0034240
     RDKit          3D
Styrene
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.6741   -0.0525    0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8759    0.4731   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    0.1899   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899   -0.6480    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -0.8836    0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.2901   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6884    0.5505   -1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    0.7860   -1.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -0.7256    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.1573    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.1448   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612   -1.1538    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -1.5534    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983   -0.4846   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    1.0388   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613    1.4512   -1.7928 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
  7  8  2  0
  8  3  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0034240 (Styrene)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.750   3.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.084   2.832   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0034240 (Styrene)

COMPND    HMDB0034240
HETATM    1  C1  UNL     1       2.674  -0.052   0.814  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.876   0.473  -0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.454   0.190  -0.113  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.190  -0.648   0.768  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.559  -0.884   0.683  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.331  -0.290  -0.285  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.688   0.550  -1.169  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.349   0.786  -1.093  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.282  -0.726   1.557  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.746   0.157   0.848  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.297   1.145  -0.807  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.361  -1.154   1.563  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.049  -1.553   1.394  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.398  -0.485  -0.337  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.287   1.039  -1.955  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.161   1.451  -1.793  1.00  0.00           H  
CONECT    1    2    2    9   10
CONECT    2    3   11
CONECT    3    4    4    8
CONECT    4    5   12
CONECT    5    6    6   13
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8   16
END
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SMILES for HMDB0034240 (Styrene)

C=CC1=CC=CC=C1
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INCHI for HMDB0034240 (Styrene)

InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC8H8
Average Molecular Weight104.1491
Monoisotopic Molecular Weight104.062600256
IUPAC Nameethenylbenzene
Traditional Namestyrene
CAS Registry Number100-42-5
SMILES
C=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2
InChI KeyPPBRXRYQALVLMV-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
  • Aromatic hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Environmental roleIndustrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-33 °CNot Available
Boiling Point145.00 to 146.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.31 mg/mL at 25 °CNot Available
LogP2.95Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-315189.153 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012552
KNApSAcK IDC00037855
Chemspider ID7220
KEGG Compound IDC19506
BioCyc IDCPD-1092
BiGG IDNot Available
Wikipedia LinkStyrene
METLIN IDNot Available
PubChem Compound7501
PDB IDNot Available
ChEBI ID27452
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029824
Good Scents IDrw1009281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roder-Stolinski C, Fischader G, Oostingh GJ, Feltens R, Kohse F, von Bergen M, Morbt N, Eder K, Duschl A, Lehmann I: Styrene induces an inflammatory response in human lung epithelial cells via oxidative stress and NF-kappaB activation. Toxicol Appl Pharmacol. 2008 Sep 1;231(2):241-7. doi: 10.1016/j.taap.2008.04.010. Epub 2008 Apr 29. [PubMed:18554678 ]
  2. Alonso S, Bartolome-Martin D, del Alamo M, Diaz E, Garcia JL, Perera J: Genetic characterization of the styrene lower catabolic pathway of Pseudomonas sp. strain Y2. Gene. 2003 Nov 13;319:71-83. [PubMed:14597173 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .