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Cyclohexane (T3D3467)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:58:32 UTC
Update Date2014-12-24 20:26:06 UTC
Accession NumberT3D3467
Identification
Common NameCyclohexane
ClassSmall Molecule
DescriptionCyclohexane is found in kohlrabi. Diluent in colour additive mixtures for food use Cyclohexane has been shown to exhibit beta-oxidant, anti-nociceptive and antibiotic functions (3, 4, 5). Cyclohexane belongs to the family of Cycloalkanes. These are alkanes containing one or more rings of carbon atoms.
Compound Type
  • Food Toxin
  • Gasoline Additive/Component
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Hexahydro-Benzene
Hexahydrobenzene
Hexamethylene
Hexanaphthene
Chemical FormulaC6H12
Average Molecular Mass84.160 g/mol
Monoisotopic Mass84.094 g/mol
CAS Registry Number110-82-7
IUPAC Namecyclohexane
Traditional Namecyclohexane
SMILESC1CCCCC1
InChI IdentifierInChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
InChI KeyInChIKey=XDTMQSROBMDMFD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains).
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassCycloalkanes
Direct ParentCycloalkanes
Alternative ParentsNot Available
Substituents
  • Cycloalkane
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point6.5°C
Boiling Point80.7°C (177.3°F)
Solubility0.055 mg/mL at 25°C
LogP3.44
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.46ALOGPS
logP2.67ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.61 m³·mol⁻¹ChemAxon
Polarizability11.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-fa371e4a0a1a00f32fb22017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-c9adeb7bca08187b71b62017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-14e97092ea29e622dae32017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-34ac8fd123caac81b7822017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-9000000000-0bd8fb51fcff3d162a792017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-fa371e4a0a1a00f32fb22018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-c9adeb7bca08187b71b62018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-14e97092ea29e622dae32018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-34ac8fd123caac81b7822018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-9000000000-0bd8fb51fcff3d162a792018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-b615c4245974ad3f563b2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-9cf791d15a6c7c1002432015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-2e3db4a621e8d150655e2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0909e8df2dab6a8a30382015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-b52cb2415db29a5e580e2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-b52cb2415db29a5e580e2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-10ba67e4fd716d27d8f72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052u-9000000000-ed8117234e8d524e8c122021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-84249c478e4c6109e4382021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-15f05f245efaabc1e46d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-8ebf781741cf0155b2cd2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-1fe2685b7f3004ca04a32021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-0ad8ca1202d0c546ee332021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a5c-9000000000-dac3fa3cc6a9fe8db32a2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (12) ; inhalation (12) ; dermal (12)
Mechanism of ToxicityPetroleum distillates are central nervous system depressants and cause pulmonary damage. (1)
MetabolismVolatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. (1)
Toxicity ValuesLD50: 1.30 g/kg (Oral, Mouse) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Cyclohexane is found in gasoline, which is possibly carcinogenic to humans (Group 2B). (13)
Uses/SourcesCyclohexane is a component of gasoline and is used as a solvent in the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon. (11)
Minimum Risk LevelNot Available
Health EffectsPetroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. They may also affect the blood, immune system, liver, and kidney. (1, 10)
SymptomsPetroleum distillate poisoning may cause nausea, vomiting, cough, pulmonary irritation progressing to pulmonary edema, bloody sputum, and bronchial pneumonia. At high amounts, central nervous system depression may also occur, with symptoms such as weakness, dizziness, slow and shallow respiration, unconsciousness, and convulsions. Petroleum distillates are also irritating to the skin. (2)
TreatmentTreatment is mainly symptomatic and supportive. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03561
HMDB IDHMDB29597
PubChem Compound ID8078
ChEMBL IDCHEMBL15980
ChemSpider ID7787
KEGG IDC11249
UniProt IDNot Available
OMIM ID
ChEBI ID29005
BioCyc IDCPD-8232
CTD IDNot Available
Stitch IDCyclohexane
PDB IDCHX
ACToR ID1847
Wikipedia LinkCyclohexane
References
Synthesis Reference

Brian J. Willis, Philip A. Christenson, Robert Mack, “Halogen containing cyclohexane derivatives, methods of preparation and compositions containing same.” U.S. Patent US4308401, issued July, 1934.

MSDSLink
General References
  1. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [16246025 ]
  2. Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [10966480 ]
  3. Tulliez JE, Durand EF, Peleran JC: Mitochondrial hydroxylation of the cyclohexane ring as a result of beta-oxidation blockade of a cyclohexyl substituted fatty acid. Lipids. 1981 Dec;16(12):888-92. [7329209 ]
  4. Haas JS, Viana AF, Heckler AP, von Poser GL, Rates SM: The antinociceptive effect of a benzopyran (HP1) isolated from Hypericum polyanthemum in mice hot-plate test is blocked by naloxone. Planta Med. 2010 Sep;76(13):1419-23. doi: 10.1055/s-0029-1240942. Epub 2010 Mar 22. [20309796 ]
  5. Randall LP, Woodward MJ: Multiple antibiotic resistance (mar) locus in Salmonella enterica serovar typhimurium DT104. Appl Environ Microbiol. 2001 Mar;67(3):1190-7. [11229910 ]
  6. Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
  7. Dreisbach, RH (1983). Handbook of Poisoning. Los Altos, California: Lange Medical Publications.
  8. MICROMEDEX Thomson Health Care (2002). USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. Englewood, CO: MICROMEDEX Thomson Health Care. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.
  9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  10. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for total petroleum hydrocarbons (TPH). U.S. Public Health Service in collaboration with U.S. [Link]
  11. Wikipedia. Cyclohexane. Last Updated 22 July 2009. [Link]
  12. Wikipedia. Lead telluride. Last Updated 8 May 2009. [Link]
  13. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Trypsin-1
General Function:
Serine-type endopeptidase activity
Specific Function:
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates.
Gene Name:
PRSS1
Uniprot ID:
P07477
Molecular Weight:
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]