MiMeDB: Showing metabocard for Benzene (MMDBc0048004)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:45:20 UTC

Update Date

2024-09-27 17:31:20 UTC

Metabolite ID

MMDBc0048004

Metabolite Identification

Common Name

Benzene

Description

Benzene 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

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

Synonyms

Value	Source
[6]Annulene	ChEBI
Benzen	ChEBI
Benzine	ChEBI
Benzol	ChEBI
Benzole	ChEBI
Bicarburet OF hydrogen	ChEBI
Coal naphtha	ChEBI
Cyclohexatriene	ChEBI
Mineral naphtha	ChEBI
Phene	ChEBI
Phenyl hydride	ChEBI
Pyrobenzol	ChEBI
Pyrobenzole	ChEBI
(6)Annulene	HMDB
Annulene	HMDB
Aromatic alkane	HMDB
Benzeen	HMDB
Benzin	HMDB
Benzinum	HMDB
Benzol 90	HMDB
Benzolene	HMDB
Benzolo	HMDB
Benzolum	HMDB
BNZ	HMDB
Carbon oil	HMDB
Fenzen	HMDB
Motor benzol	HMDB
Polystream	HMDB
RNG	HMDB
{[6]annulene}	HMDB

Molecular Formula

C₆H₆

Average Mass

78.1118

Monoisotopic Mass

78.046950192

IUPAC Name

benzene

Traditional Name

benzene

CAS Registry Number

Not Available

SMILES

C1=CC=CC=C1

InChI Identifier

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

InChI Key

UHOVQNZJYSORNB-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenes (CHEBI:16716 )
aromatic annulene (CHEBI:16716 )
an aromatic compound (BENZENE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	2.03	ALOGPS
logP	1.97	ChemAxon
logS	-1.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.06 m³·mol⁻¹	ChemAxon
Polarizability	8.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-70967112fec69784847c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-92ccc664b07cb6c56de9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-9100000000-11f8463e7c6286637b1b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-70967112fec69784847c	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-92ccc664b07cb6c56de9	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-9100000000-11f8463e7c6286637b1b	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-c5901591488019f3ac5d	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004i-9000000000-70967112fec69784847c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-004i-9000000000-92ccc664b07cb6c56de9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positive	splash10-004i-9100000000-11f8463e7c6286637b1b	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-45ac36cbb443a00d6a17	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-9cad19d98e6420c7b6a3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-2dace4807cb04a7942de	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-b9df9bb9660e1fc49a7f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b4ff542394722302be43	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-b961755486c61c33c1c7	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-9000000000-9a8a4f7775597a0e167e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-fd85b2b474c37c371a5a	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9000000000-08f396d6cb4660e57caa	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Bone Marrow
Breath
Epidermis
Feces
Leukocyte
Liver
Saliva

Tissue Locations

Bone Marrow
Epidermis
Leukocyte
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Data Source	Reference
Hepatitis	PubMed	12071572
Leukemia	PubMed	31017485; 23066403
Hepatitis	PubMed	12071572
Genotoxic	PubMed	29070767
Carcinogenic	PubMed	29107678; 3053447; 21259300

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human ; Human feces

Exposure Sources

Source Type	Species	Data Source	Reference
Plant	Common bean	FooDB	31437929
Plant	Safflower	FooDB	31437929
Plant	Lovage	FooDB	31437929
Plant	Blackberry	FooDB	31437929
Plant	Guava	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.000307	0.000256	0.000384	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Blood	Detected and Quantified	0.000384	0.000320	0.000448	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Bone marrow	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Saliva	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24657864
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Breath	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24086492

External Links

HMDB ID

HMDB0001505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzene

METLIN ID

6285

PubChem Compound

241

PDB ID

Not Available

ChEBI ID

16716

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1093/carcin/16.7.1519. [PubMed:7614685 ]
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. doi: 10.1002/(SICI)1097-0274(199603)29:3<236::AID-AJIM3>3.0.CO;2-O. [PubMed:8833776 ]
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. doi: 10.1002/(SICI)1097-0274(199603)29:3<247::AID-AJIM4>3.0.CO;2-N. [PubMed:8833777 ]
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. doi: 10.1093/carcin/18.4.817. [PubMed:9111220 ]
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. doi: 10.1289/ehp.961041211. [PubMed:9118895 ]
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. doi: 10.1289/ehp.961041247. [PubMed:9118900 ]
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. doi: 10.1289/ehp.961041289. [PubMed:9118908 ]
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. doi: 10.1016/s0145-2126(97)00157-4. [PubMed:9593466 ]
Barbera N, Bulla G, Romano G: A fatal case of benzene poisoning. J Forensic Sci. 1998 Nov;43(6):1250-1. [PubMed:9846407 ]
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. doi: 10.1016/s0048-9697(99)00197-7. [PubMed:10535123 ]
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 ]
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. doi: 10.2486/indhealth.39.206. [PubMed:11341554 ]
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 ]
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 ]
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 ]
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. doi: 10.1080/10428190410001693515. [PubMed:15370219 ]
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. doi: 10.1002/em.20146. [PubMed:15920754 ]
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. doi: 10.1016/j.leukres.2005.08.019. Epub 2005 Sep 23. [PubMed:16183116 ]
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. doi: 10.1016/j.toxlet.2005.09.017. Epub 2005 Oct 19. [PubMed:16242870 ]
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. doi: 10.1073/pnas.0508573102. Epub 2005 Nov 14. [PubMed:16286641 ]

Showing metabocard for Benzene (MMDBc0048004)

MOL for #<Metabolite:0x00007f46e8652e68>

3D MOL for #<Metabolite:0x00007f46e8652e68>

3D SDF for #<Metabolite:0x00007f46e8652e68>

3D-SDF for #<Metabolite:0x00007f46e8652e68>

PDB for #<Metabolite:0x00007f46e8652e68>

3D PDB for #<Metabolite:0x00007f46e8652e68>

SMILES for #<Metabolite:0x00007f46e8652e68>

INCHI for #<Metabolite:0x00007f46e8652e68>

Structure for #<Metabolite:0x00007f46e8652e68>

3D Structure for #<Metabolite:0x00007f46e8652e68>