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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:50:31 UTC

Update Date

2022-03-07 02:53:23 UTC

HMDB ID

HMDB0032566

Secondary Accession Numbers

HMDB32566

Metabolite Identification

Common Name

Hexachlorobenzene

Description

Hexachlorobenzene, also known as no bunt or HCB, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Hexachlorobenzene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Hexachlorobenzene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Hexachlorobenzene.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM   10 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5    9                                                  
CONECT    4    2    6   10                                                  
CONECT    5    3    6   11                                                  
CONECT    6    4    5   12                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4,5,6-Hexachlorobenzene	ChEBI
HCB	ChEBI
Hexachlorbenzol	ChEBI
Perchlorobenzene	ChEBI
Phenyl perchloryl	ChEBI
1,2,3,4,5,6-Hexachloro-benzene	HMDB
Amatin	HMDB
Anticarie	HMDB
Bunt-cure	HMDB
Bunt-NO-more	HMDB
Ceku c.b	HMDB
Ceku c.b.	HMDB
CO-OP Hexa	HMDB
Esaclorobenzene	HMDB
Granox	HMDB
Granox NM	HMDB
Hexa c.b	HMDB
Hexa c.b.	HMDB
Hexa CB	HMDB
Hexachloro-benzene	HMDB
Hexcachlorbenzen	HMDB
Julen'S carbon chloride	HMDB
Julian'S carbon chloride	HMDB
Julin'S carbon chloride	HMDB
Julin'S chloride	HMDB
No bunt	HMDB
No bunt 40	HMDB
No bunt 80	HMDB
No bunt liquid	HMDB
Pentachlorophenyl chloride	HMDB
S Anocide	HMDB
Saatbeizfungizid	HMDB
Sanocid	HMDB
Sanocide	HMDB
Smut-go	HMDB
Snieciotox	HMDB
Voronit c	HMDB

Chemical Formula

C₆Cl₆

Average Molecular Weight

284.782

Monoisotopic Molecular Weight

281.813116242

IUPAC Name

hexachlorobenzene

Traditional Name

hexachlorobenzene

CAS Registry Number

118-74-1

SMILES

ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl

InChI Identifier

InChI=1S/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9

InChI Key

CKAPSXZOOQJIBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic fungicide (CHEBI:5692 )
chlorobenzenes (CHEBI:5692 )
Organochlorine fungicides (C11042 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0032566)

Cellular substructure

Membrane (HMDB: HMDB0032566)
Cell membrane (HMDB: HMDB0032566)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0032566)
Inhalation (HMDB: HMDB0032566)

Enteral

Ingestion (HMDB: HMDB0032566)

Source

Endogenous

Endogenous (HMDB: HMDB0032566)

Exogenous

Food

Food (HMDB: HMDB0032566)

Synthetic

Synthetic (HMDB: HMDB0032566)

Environmental

Sludge (HMDB: HMDB0032566)

Exogenous (HMDB: HMDB0032566)

Process

Not Available

Role

Indirect biological role

Carcinogen (HMDB: HMDB0032566)
Persistent organic pollutant (HMDB: HMDB0032566)

Environmental role

Air pollutant (HMDB: HMDB0032566)

Industrial application

Agrochemical (HMDB: HMDB0032566)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0032566)
Fungicide (HMDB: HMDB0032566)

Pesticide (HMDB: HMDB0032566)

Biological role

Carcinogenic agent (HMDB: HMDB0032566)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	226 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.2e-06 mg/mL at 25 °C	Not Available
LogP	5.73	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	5.7	ALOGPS
logP	5.6	ChemAxon
logS	-6.2	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	54.89 m³·mol⁻¹	ChemAxon
Polarizability	21.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.989	30932474
DeepCCS	[M-H]-	144.631	30932474
DeepCCS	[M-2H]-	179.785	30932474
DeepCCS	[M+Na]+	155.323	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.6	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	111.5	32859911
AllCCS	[M+Na-2H]-	111.9	32859911
AllCCS	[M+HCOO]-	112.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.03 minutes	32390414
Predicted by Siyang on May 30, 2022	25.0029 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.73 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3107.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1033.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	405.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	824.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1022.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1197.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1350.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1953.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	799.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2261.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	865.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	820.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1461.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	685.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	582.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexachlorobenzene	ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl	2279.4	Standard polar	33892256
Hexachlorobenzene	ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl	1695.9	Standard non polar	33892256
Hexachlorobenzene	ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl	1711.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene GC-MS (Non-derivatized)	splash10-05au-3890000000-f69d8d041047bbbd8cf6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene EI-B (Non-derivatized)	splash10-001r-0390000000-97dc8f4d1e5fb325407e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene EI-B (Non-derivatized)	splash10-0019-1390000000-e4057ffa68f36abf1e5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene EI-B (Non-derivatized)	splash10-001r-0290000000-be7d6414f99da634dbcc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene GC-MS (Non-derivatized)	splash10-05au-3890000000-f69d8d041047bbbd8cf6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexachlorobenzene GC-EI-TOF (Non-derivatized)	splash10-0537-1980000000-4d496eb3ebb555f0d5d2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexachlorobenzene GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-0090000000-dd5c6fd778459bb7b727	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexachlorobenzene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001r-1490000000-0dacd4ae21bcd544d5a2	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 10V, Positive-QTOF	splash10-001i-0090000000-ac24e2bc100359502cbc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 20V, Positive-QTOF	splash10-001i-0090000000-ac24e2bc100359502cbc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 40V, Positive-QTOF	splash10-001i-0090000000-ac24e2bc100359502cbc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 10V, Negative-QTOF	splash10-001i-0090000000-e8ac20108d55e4950623	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 20V, Negative-QTOF	splash10-001i-0090000000-e8ac20108d55e4950623	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 40V, Negative-QTOF	splash10-001i-0090000000-e8ac20108d55e4950623	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 10V, Positive-QTOF	splash10-001i-0090000000-c0992f2959227d61d8be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 20V, Positive-QTOF	splash10-001i-0090000000-c0992f2959227d61d8be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexachlorobenzene 40V, Positive-QTOF	splash10-001i-0090000000-c0992f2959227d61d8be	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00025(0.00021-0.00032) uM	Adult (>18 years old)	Both	Normal	Report on Human B...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010498

KNApSAcK ID

Not Available

Chemspider ID

8067

KEGG Compound ID

C11042

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexachlorobenzene

METLIN ID

Not Available

PubChem Compound

8370

PDB ID

Not Available

ChEBI ID

5692

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hao L, Xue J: Multiresidue analysis of 18 organochlorine pesticides in traditional chinese medicine. J Chromatogr Sci. 2006 Sep;44(8):518-22. [PubMed:16959129 ]
Graifemberghi S, Gavazzoni R, Pozzo G, Callea F, Pizzoli G: [Chloroquine-induced lesions in the liver of healthy rats and rats with porphyria induced by hexachlorobenzene]. G Ital Dermatol Venereol. 1982 May-Jun;117(3):149-54. [PubMed:7187393 ]
Xue J, Hao L, Peng F: Residues of 18 organochlorine pesticides in 30 traditional Chinese medicines. Chemosphere. 2008 Apr;71(6):1051-5. Epub 2007 Dec 26. [PubMed:18160094 ]
Chernev K, Ivanov E, Adzharov D: [Induction of mixed microsomal oxidase in experimental hexachlorobenzene porphyria in rabbits]. Eksp Med Morfol. 1981;20(1):8-11. [PubMed:6112130 ]
Polese L, Ribeiro ML: Methods for determination of hexachlorobenzene and pentachlorophenol in soil samples. Talanta. 1998 Aug;46(5):915-20. [PubMed:18967213 ]
Michielsen C, Boeren S, Rietjens I, van Mil F, Vos J, Bloksma N: The mercapturic acid biotransformation pathway of hexachlorobenzene is not involved in the induction of splenomegaly, or skin and lung lesions in the Brown Norway rat. Arch Toxicol. 2000 Dec;74(10):609-17. [PubMed:11201668 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Hexachlorobenzene (HMDB0032566)

MOL for HMDB0032566 (Hexachlorobenzene)

3D MOL for HMDB0032566 (Hexachlorobenzene)

3D SDF for HMDB0032566 (Hexachlorobenzene)

3D-SDF for HMDB0032566 (Hexachlorobenzene)

PDB for HMDB0032566 (Hexachlorobenzene)

3D PDB for HMDB0032566 (Hexachlorobenzene)

SMILES for HMDB0032566 (Hexachlorobenzene)

INCHI for HMDB0032566 (Hexachlorobenzene)

Structure for HMDB0032566 (Hexachlorobenzene)

3D Structure for HMDB0032566 (Hexachlorobenzene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra