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Showing NP-Card for Benzene (NP0001207)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-24 13:18:08 UTC
NP-MRD IDNP0001207
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001207 (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 NP0001207 (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 NP0001207 (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>
NP0001207

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0001207 (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
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PDB for NP0001207 (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 NP0001207 (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 NP0001207 (Benzene)

C1=CC=CC=C1
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INCHI for NP0001207 (Benzene)

InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
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View in JSmol
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 Mass78.1118 Da
Monoisotopic Mass78.04695 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ananas comosusLOTUS Database
Basella albaLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Carthamus tinctoriusFooDB
Citrus limonLOTUS Database
Cynara cardunculusLOTUS Database
Elsholtzia ciliataLOTUS Database
Juglans nigraLOTUS Database
Levisticum officinaleFooDB
Manilkara zapotaLOTUS Database
Phaseolus vulgarisFooDB
Psidium guajavaFooDB
Swertia japonicaLOTUS Database
Telosma procumbensKNApSAcK Database
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
Physical Properties
StateLiquid
Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted 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
HMDB IDHMDB0001505
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1221761
References
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 ]
  21. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed:1234 ]