| Record Information |
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| Version | 1.0 |
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| Creation Date | 2018-10-03 16:32:54 UTC |
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| Update Date | 2020-06-04 18:57:41 UTC |
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| MCDB ID | BMDB0063606 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | delta-Hexachlorocyclohexane |
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| Description | Delta-hexachlorocyclohexane (delta-HCH) is a solid. It is a component of technical grade HCH. The interaction of delta-HCH with human red blood cells disrupts membrane structure and changes the environment of cytoskeleton proteins that could cause cell lysis. No neoplastic or nonneoplastic effects were noted in livers of male mice or rats given dietary delta-HCH at concentrations ranging from 100-1000 ppm. delta-HCH was particularly potent toward disrupting Ca2+ homeostasis in a variety of excitable and nonexcitable cells and altering contractility of cardiac muscle. delta-HCH interacts with cardiac ryanodine-sensitive Ca2+ channels (RyR2), accounting in part for altered Ca2+ transients and contractility. delta-HCH increases the ionic permeability of phospholipid membranes by two distinct Ca2+-dependent mechanisms: one mediated through RyR and the other mediated by a unique ionophore activity. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (1alpha,2alpha,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-Hexachlorocyclohexane | ChEBI | | (1R,2C,3C,4t,5C,6t)-1,2,3,4,5,6-Hexachlorocyclohexane | ChEBI | | delta-Benzene hexachloride | ChEBI | | delta-BHC | ChEBI | | delta-Lindane | ChEBI | | (1a,2a,3a,4b,5a,6b)-1,2,3,4,5,6-Hexachlorocyclohexane | Generator | | (1Α,2α,3α,4β,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexane | Generator | | Δ-benzene hexachloride | Generator | | Δ-BHC | Generator | | Δ-lindane | Generator | | Δ-hexachlorocyclohexane | Generator |
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| Chemical Formula | C6H6Cl6 |
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| Average Molecular Weight | 290.83 |
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| Monoisotopic Molecular Weight | 287.860066434 |
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| IUPAC Name | (1R,2S,3r,4R,5S,6s)-1,2,3,4,5,6-hexachlorocyclohexane |
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| Traditional Name | delta-BHC |
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| CAS Registry Number | 319-86-8 |
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| SMILES | [H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@]([H])(Cl)[C@]1([H])Cl |
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| InChI Identifier | InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5-,6- |
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| InChI Key | JLYXXMFPNIAWKQ-GPIVLXJGSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organohalogen compounds |
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| Class | Alkyl halides |
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| Sub Class | Cyclohexyl halides |
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| Direct Parent | Cyclohexyl halides |
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| Alternative Parents | |
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| Substituents | - Cyclohexyl halide
- Hydrocarbon derivative
- Organochloride
- Alkyl chloride
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-a80ad4b803c6cfbad7f9 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0190000000-94757a7ebf0ca8417382 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000f-4590000000-a1b5e62bd325a4408726 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-094eac0e1195e28c6f04 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-b09c755105529e48aaa9 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-0090000000-ee4766742eba17f9525e | 2016-08-03 | View Spectrum |
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| Concentrations |
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| Detected and Quantified | 0.0014 +/- 0.00413 uM | | | details |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | Not Available |
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| PDB ID | Not Available |
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| ChEBI ID | 39095 |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16. [PubMed:17180431 ]
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