HEXANE

General Information

MaintermHEXANE
Doc TypeASP
CAS Reg.No.(or other ID)110-54-3
Regnum 175.105
175.320
177.1200
176.200
73.295
73.30
73.345
73.615
172.560
73.300
172.340
173.270
73.315

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID8058
IUPAC Namehexane
InChIInChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
InChI KeyVLKZOEOYAKHREP-UHFFFAOYSA-N
Canonical SMILESCCCCCC
Molecular FormulaC6H14
Wikipediahexane

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight86.178
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count3
Complexity12.0
CACTVS Substructure Key Fingerprint A A A D c c B g A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G A A A A A A A C A C A A A A C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A I A A A A A A A A A A A A A A A E A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area0.0
Monoisotopic Mass86.11
Exact Mass86.11
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9861
Human Intestinal AbsorptionHIA+0.9906
Caco-2 PermeabilityCaco2+0.8324
P-glycoprotein SubstrateNon-substrate0.6733
P-glycoprotein InhibitorNon-inhibitor0.9136
Non-inhibitor0.8647
Renal Organic Cation TransporterNon-inhibitor0.8920
Distribution
Subcellular localizationLysosome0.5774
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8362
CYP450 2D6 SubstrateNon-substrate0.7703
CYP450 3A4 SubstrateNon-substrate0.7155
CYP450 1A2 InhibitorNon-inhibitor0.6163
CYP450 2C9 InhibitorNon-inhibitor0.9361
CYP450 2D6 InhibitorNon-inhibitor0.9302
CYP450 2C19 InhibitorNon-inhibitor0.9464
CYP450 3A4 InhibitorNon-inhibitor0.9870
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7973
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9026
Non-inhibitor0.8340
AMES ToxicityNon AMES toxic0.9950
CarcinogensCarcinogens 0.6584
Fish ToxicityHigh FHMT0.8414
Tetrahymena Pyriformis ToxicityHigh TPT0.9253
Honey Bee ToxicityHigh HBT0.7493
BiodegradationReady biodegradable0.7562
Acute Oral ToxicityIV0.5031
Carcinogenicity (Three-class)Non-required0.5951

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.9238LogS
Caco-2 Permeability1.5290LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.3046LD50, mol/kg
Fish Toxicity0.5231pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.4327pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureOral ; inhalation ;dermal
Mechanism of ToxicityHexane's toxicity is caused by it neurotoxic metabolite, 2,5-hexanedione. It damages the central and peripheral nervous system by causing axonal swelling and degeneration. 2,5-Hexanedione also reacts with lysine side-chain amino groups in axonal cytoskeletal proteins to form pyrroles. This results in neurofilament cross-linking and loss of function.
MetabolismHexane is mainly absorbed via inhalation, as it is readily absorbed by the lungs. It is distributed throughout the body in the blood, and metabolized by mixed function oxidases in the liver to a number of metabolites. The initial reaction is oxidation by cytochrome P-450 isozymes to hexanols, predominantly 2-hexanol. Further reactions convert 2-hexanol to 2-hexanone, 2,5-hexanediol, 5-hydroxy-2-hexanone, 4,5-dihydroxy-2-hexanone and the neurotoxicant 2,5-hexanedione. Hexane metabolites are excreted in the urine, while unchanged hexane is excreted in expired air.
Toxicity ValuesLD50: 28 710 mg/kg (Oral, Rat) LC50: 48 000 ppm over 4 hours (Inhalation, Mouse)
Lethal Dose50 grams for an adult human.
Carcinogenicity (IARC Classification)Hexane is found in gasoline, which is possibly carcinogenic to humans (Group 2B).
Minimum Risk LevelChronic Inhalation: 0.6 ppm
Health EffectsHexane mainly affects the nervous system. It causes degeneration of the peripheral nervous system (and eventually the central nervous system), starting with damage to the nerve axons. Exposure to hexane may also damage the lungs and reproductive system. (L977, L978)
TreatmentNone
Reference
  1. Meulenberg CJ, Vijverberg HP: Selective inhibition of gamma-aminobutyric acid type A receptors in human IMR-32 cells by low concentrations of toluene. Toxicology. 2003 Aug 28;190(3):243-8.[12927378 ]
  2. Rathi A, Srivastava AK, Shirwaikar A, Singh Rawat AK, Mehrotra S: Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine. Phytomedicine. 2008 Jun;15(6-7):470-7. doi: 10.1016/j.phymed.2007.11.010. Epub 2008 Mar 4.[18164606 ]
  3. Wiart C, Hannah A, Yusof M, Hamimah H, Sulaiman M: Growth inhibition of foodborne and nosocomial pathogens by aqueous fraction of bearded Argostemma (Argostemma involucratum Hemsl., Rubiaceae). J Herb Pharmacother. 2005;5(3):97-102.[16520301 ]
  4. Freitas CS, Baggio CH, Dos Santos AC, Mayer B, Twardowschy A, Luiz AP, Marcon R, Soldi C, Pizzolatti MG, Dos Santos EP, Marques MC, Santos AR: Antinociceptive properties of the hydroalcoholic extract, fractions and compounds obtained from the aerial parts of Baccharis illinita DC in mice. Basic Clin Pharmacol Toxicol. 2009 Apr;104(4):285-92. doi: 10.1111/j.1742-7843.2008.00367.x. Epub 2009 Mar 5.[19281601 ]
  5. Villena C, Vivas JM, Villar AM: Suppression of croton oil-induced rabbit corneal edema by sideritis javalambrensis. J Ethnopharmacol. 2000 Jul;71(1-2):301-5.[10904177 ]
  6. Kunle O, Okogun J, Egamana E, Emojevwe E, Shok M: Antimicrobial activity of various extracts and carvacrol from Lippia multiflora leaf extract. Phytomedicine. 2003 Jan;10(1):59-61.[12622465 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassHydrocarbons
ClassSaturated hydrocarbons
SubclassAlkanes
Intermediate Tree NodesNot available
Direct ParentAlkanes
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsAcyclic alkane - Alkane - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.

From ClassyFire

Targets

Target Details

Myelin basic protein

General Function:
Structural constituent of myelin sheath
Specific Function:
The classic group of MBP isoforms (isoform 4-isoform 14) are with PLP the most abundant protein components of the myelin membrane in the CNS. They have a role in both its formation and stabilization. The smaller isoforms might have an important role in remyelination of denuded axons in multiple sclerosis. The non-classic group of MBP isoforms (isoform 1-isoform 3/Golli-MBPs) may preferentially have a role in the early developing brain long before myelination, maybe as components of transcriptional complexes, and may also be involved in signaling pathways in T-cells and neural cells. Differential splicing events combined with optional post-translational modifications give a wide spectrum of isomers, with each of them potentially having a specialized function. Induces T-cell proliferation.
Gene Name:
MBP
Uniprot ID:
P02686
Molecular Weight:
33116.855 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]
Target Details

Neurofilament heavy polypeptide

General Function:
Toxic substance binding
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber. NF-H has an important function in mature axons that is not subserved by the two smaller NF proteins.
Gene Name:
NEFH
Uniprot ID:
P12036
Molecular Weight:
112477.915 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. : http://en.wikipedia.org/wiki/Methanol
Target Details

Neurofilament light polypeptide

General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFL
Uniprot ID:
P07196
Molecular Weight:
61515.95 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. : http://en.wikipedia.org/wiki/Methanol
Target Details

Neurofilament medium polypeptide

General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFM
Uniprot ID:
P07197
Molecular Weight:
102471.425 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. : http://en.wikipedia.org/wiki/Methanol
Target Details

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. 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 ]
Target Details

Glycolipid transfer protein

General Function:
Lipid binding
Specific Function:
Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides.
Gene Name:
GLTP
Uniprot ID:
Q9NZD2
Molecular Weight:
23849.6 Da
References
  1. 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 ]

From T3DB