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Showing metabocard for Benzene (HMDB0001505)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001505
Secondary Accession Numbers
  • HMDB01505
Metabolite Identification
Common NameBenzene
DescriptionBenzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene, also known as benzol or [6]annulene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene is a natural constituent of crude oil and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. It is sometimes abbreviated PhH. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma around petrol (gasoline) stations. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although a major industrial chemical, benzene finds limited use in consumer items because of its toxicity. Benzene is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Benzene has been found to be associated with several diseases such as autism and pervasive developmental disorder not otherwise specified.
Structure
Data?1582752206
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001505 (Benzene)


  Mrv1652303202019012D          

  6  6  0  0  0  0            999 V2000
   -0.8705    0.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    0.0777    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
M  END
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3D MOL for HMDB0001505 (Benzene)

HMDB0001505
     RDKit          3D
Benzene
 12 12  0  0  0  0  0  0  0  0999 V2000
   -1.3510   -0.2194    0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5184   -1.3101   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -1.0692   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.2119   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5116    1.3013    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485    1.0740    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -0.3969    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -2.3259   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -1.9123   -0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250    0.3993   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    2.3226    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.9246    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
M  END
Download

3D SDF for HMDB0001505 (Benzene)


  Mrv1652303202019012D          

  6  6  0  0  0  0            999 V2000
   -0.8705    0.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    0.0777    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
M  END
> <DATABASE_ID>
HMDB0001505

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H

> <INCHI_KEY>
UHOVQNZJYSORNB-UHFFFAOYSA-N

> <FORMULA>
C6H6

> <MOLECULAR_WEIGHT>
78.1118

> <EXACT_MASS>
78.046950192

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.891672212088666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.973245816

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
26.058

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001505 (Benzene)

HMDB0001505
     RDKit          3D
Benzene
 12 12  0  0  0  0  0  0  0  0999 V2000
   -1.3510   -0.2194    0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5184   -1.3101   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -1.0692   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.2119   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5116    1.3013    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485    1.0740    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -0.3969    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -2.3259   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -1.9123   -0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250    0.3993   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    2.3226    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.9246    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
M  END
Download

PDB for HMDB0001505 (Benzene)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.625   0.915   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.958   0.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.958  -1.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.625  -2.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.291  -1.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.291   0.145   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                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for HMDB0001505 (Benzene)

COMPND    HMDB0001505
HETATM    1  C1  UNL     1      -1.351  -0.219   0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.518  -1.310  -0.121  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.840  -1.069  -0.147  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.341   0.212  -0.028  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.512   1.301   0.120  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.848   1.074   0.148  1.00  0.00           C  
HETATM    7  H1  UNL     1      -2.408  -0.397   0.049  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.863  -2.326  -0.217  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.516  -1.912  -0.263  1.00  0.00           H  
HETATM   10  H4  UNL     1       2.425   0.399  -0.049  1.00  0.00           H  
HETATM   11  H5  UNL     1       0.870   2.323   0.217  1.00  0.00           H  
HETATM   12  H6  UNL     1      -1.515   1.925   0.264  1.00  0.00           H  
CONECT    1    2    2    6    7
CONECT    2    3    8
CONECT    3    4    4    9
CONECT    4    5   10
CONECT    5    6    6   11
CONECT    6   12
END
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SMILES for HMDB0001505 (Benzene)

C1=CC=CC=C1
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INCHI for HMDB0001505 (Benzene)

InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
[6]AnnuleneChEBI
BenzenChEBI
BenzineChEBI
BenzolChEBI
BenzoleChEBI
Bicarburet OF hydrogenChEBI
Coal naphthaChEBI
CyclohexatrieneChEBI
Mineral naphthaChEBI
PheneChEBI
Phenyl hydrideChEBI
PyrobenzolChEBI
PyrobenzoleChEBI
(6)AnnuleneHMDB
AnnuleneHMDB
Aromatic alkaneHMDB
BenzeenHMDB
BenzinHMDB
BenzinumHMDB
Benzol 90HMDB
BenzoleneHMDB
BenzoloHMDB
BenzolumHMDB
BNZHMDB
Carbon oilHMDB
FenzenHMDB
Motor benzolHMDB
PolystreamHMDB
RNGHMDB
{[6]annulene}HMDB
Chemical FormulaC6H6
Average Molecular Weight78.1118
Monoisotopic Molecular Weight78.046950192
IUPAC Namebenzene
Traditional Namebenzene
CAS Registry Number71-43-2
SMILES
C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
InChI KeyUHOVQNZJYSORNB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5.5 °CNot Available
Boiling Point80.00 to 81.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.79 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP2.03ALOGPS
logP1.97ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.06 m³·mol⁻¹ChemAxon
Polarizability8.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+111.27631661259
DarkChem[M-H]-105.84331661259
AllCCS[M+H]+113.43332859911
AllCCS[M-H]-112.76932859911
DeepCCS[M+H]+119.18730932474
DeepCCS[M-H]-116.88530932474
DeepCCS[M-2H]-152.7630932474
DeepCCS[M+Na]+127.37530932474
AllCCS[M+H]+113.432859911
AllCCS[M+H-H2O]+108.132859911
AllCCS[M+NH4]+118.532859911
AllCCS[M+Na]+119.932859911
AllCCS[M-H]-112.832859911
AllCCS[M+Na-2H]-116.432859911
AllCCS[M+HCOO]-120.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzeneC1=CC=CC=C1954.0Standard polar33892256
BenzeneC1=CC=CC=C1670.4Standard non polar33892256
BenzeneC1=CC=CC=C1661.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzene CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-c5901591488019f3ac5d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-08f396d6cb4660e57caa2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzene EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-004i-9000000000-70967112fec69784847c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzene EI-B (JEOL JMS-D-3000) , Positive-QTOFsplash10-004i-9000000000-92ccc664b07cb6c56de92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzene EI-B (HP 5970) , Positive-QTOFsplash10-0fb9-9000000000-2aae37aac9f2a02d5e8b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzene CI-B (FINNIGAN-MAT 4500) , Positive-QTOFsplash10-004i-9100000000-11f8463e7c6286637b1b2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 10V, Positive-QTOFsplash10-004i-9000000000-45ac36cbb443a00d6a172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 20V, Positive-QTOFsplash10-004i-9000000000-9cad19d98e6420c7b6a32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 40V, Positive-QTOFsplash10-004i-9000000000-2dace4807cb04a7942de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 10V, Negative-QTOFsplash10-004i-9000000000-b9df9bb9660e1fc49a7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 20V, Negative-QTOFsplash10-004i-9000000000-b9df9bb9660e1fc49a7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 40V, Negative-QTOFsplash10-004i-9000000000-b4ff542394722302be432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 10V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 20V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 40V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 10V, Positive-QTOFsplash10-004i-9000000000-b961755486c61c33c1c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 20V, Positive-QTOFsplash10-0fb9-9000000000-9a8a4f7775597a0e167e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzene 40V, Positive-QTOFsplash10-004i-9000000000-fd85b2b474c37c371a5a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
Tissue Locations
  • Bone Marrow
  • Epidermis
  • Leukocyte
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000384 (0.000320-0.000448) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
BloodDetected and Quantified0.000307 (0.000256-0.000384) uMChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012843
KNApSAcK IDC00033435
Chemspider ID236
KEGG Compound IDC01407
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzene
METLIN ID6285
PubChem Compound241
PDB IDNot Available
ChEBI ID16716
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1221761
References
Synthesis ReferenceCopisarow, Maurice; Long, Cyril N H. The Friedel-Crafts' reaction. II. Migration of halogen atoms in the benzene nucleus. Journal of the Chemical Society, Transactions (1921), 119 442-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wiwanitkit V, Soogarun S, Suwansaksri J: Urine phenol and myeloperoxidase index: an observation in benzene exposed subjects. Leuk Lymphoma. 2004 Aug;45(8):1643-5. [PubMed:15370219 ]
  2. Wang S, Chen H, Wang X: [Studies on relationship between exposure to low concentration of mixed benzene and lower quality of semen and very early fetal loss]. Zhonghua Yu Fang Yi Xue Za Zhi. 2000 Sep;34(5):271-3. [PubMed:11372393 ]
  3. Zhang L, Wang Y, Shang N, Smith MT: Benzene metabolites induce the loss and long arm deletion of chromosomes 5 and 7 in human lymphocytes. Leuk Res. 1998 Feb;22(2):105-13. [PubMed:9593466 ]
  4. Fabiani R, De Bartolomeo A, Morozzi G: Involvement of oxygen free radicals in the serum-mediated increase of benzoquinone genotoxicity. Environ Mol Mutagen. 2005 Oct;46(3):156-63. [PubMed:15920754 ]
  5. Turteltaub KW, Mani C: Benzene metabolism in rodents at doses relevant to human exposure from urban air. Res Rep Health Eff Inst. 2003 Feb;(113):1-26; discussion 27-35. [PubMed:12675491 ]
  6. Irons RD, Stillman WS: Impact of benzene metabolites on differentiation of bone marrow progenitor cells. Environ Health Perspect. 1996 Dec;104 Suppl 6:1247-50. [PubMed:9118900 ]
  7. Rothman N, Li GL, Dosemeci M, Bechtold WE, Marti GE, Wang YZ, Linet M, Xi LQ, Lu W, Smith MT, Titenko-Holland N, Zhang LP, Blot W, Yin SN, Hayes RB: Hematotoxicity among Chinese workers heavily exposed to benzene. Am J Ind Med. 1996 Mar;29(3):236-46. [PubMed:8833776 ]
  8. Barbera N, Bulla G, Romano G: A fatal case of benzene poisoning. J Forensic Sci. 1998 Nov;43(6):1250-1. [PubMed:9846407 ]
  9. Rolle-Kampczyk UE, Rehwagen M, Franck U, Weiss H, Krumbiegel P, Herbarth O: Bio-effect monitoring using a [(15)N]methacetin test as diagnostic tool to monitor remediation effects in an industrially polluted region. Toxicol Lett. 2006 Apr 10;162(2-3):234-8. Epub 2005 Oct 19. [PubMed:16242870 ]
  10. Vermeulen R, Lan Q, Zhang L, Gunn L, McCarthy D, Woodbury RL, McGuire M, Podust VN, Li G, Chatterjee N, Mu R, Yin S, Rothman N, Smith MT: Decreased levels of CXC-chemokines in serum of benzene-exposed workers identified by array-based proteomics. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17041-6. Epub 2005 Nov 14. [PubMed:16286641 ]
  11. Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504. [PubMed:10570033 ]
  12. Gut I, Nedelcheva V, Soucek P, Stopka P, Tichavska B: Cytochromes P450 in benzene metabolism and involvement of their metabolites and reactive oxygen species in toxicity. Environ Health Perspect. 1996 Dec;104 Suppl 6:1211-8. [PubMed:9118895 ]
  13. Irons RD, Lv L, Gross SA, Ye X, Bao L, Wang XQ, Ryder J, Armstrong TW, Zhou Y, Miao L, Le AT, Kerzic PJ, Ni W, Fu H: Chronic exposure to benzene results in a unique form of dysplasia. Leuk Res. 2005 Dec;29(12):1371-80. Epub 2005 Sep 23. [PubMed:16183116 ]
  14. Xiao G, Pan C, Cai Y, Lin H, Fu Z: Effect of benzene, toluene, xylene on the semen quality and the function of accessory gonad of exposed workers. Ind Health. 2001 Apr;39(2):206-10. [PubMed:11341554 ]
  15. Dees C, Askari M, Henley D: Carcinogenic potential of benzene and toluene when evaluated using cyclin-dependent kinase activation and p53-DNA binding. Environ Health Perspect. 1996 Dec;104 Suppl 6:1289-92. [PubMed:9118908 ]
  16. Ward E, Hornung R, Morris J, Rinsky R, Wild D, Halperin W, Guthrie W: Risk of low red or white blood cell count related to estimated benzene exposure in a rubberworker cohort (1940-1975) Am J Ind Med. 1996 Mar;29(3):247-57. [PubMed:8833777 ]
  17. Seaton MJ, Schlosser P, Medinsky MA: In vitro conjugation of benzene metabolites by human liver: potential influence of interindividual variability on benzene toxicity. Carcinogenesis. 1995 Jul;16(7):1519-27. [PubMed:7614685 ]
  18. Brugnone F, Perbellini L, Romeo L, Cerpelloni M, Bianchin M, Tonello A: Benzene in blood as a biomarker of low level occupational exposure. Sci Total Environ. 1999 Sep 1;235(1-3):247-52. [PubMed:10535123 ]
  19. Ress NB: NTP Technical Report on the metabolism, toxicity and predicted carcinogenicity of diazoaminobenzene (CAS No. 136-35-6). Toxic Rep Ser. 2002 Sep;(73):1-23, A1-C6. [PubMed:12370695 ]
  20. Surralles J, Autio K, Nylund L, Jarventaus H, Norppa H, Veidebaum T, Sorsa M, Peltonen K: Molecular cytogenetic analysis of buccal cells and lymphocytes from benzene-exposed workers. Carcinogenesis. 1997 Apr;18(4):817-23. [PubMed:9111220 ]