Octane (T3D3440)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-07-30 17:58:18 UTC
Update Date2014-12-24 20:26:03 UTC
Accession NumberT3D3440
Identification
Common NameOctane
ClassSmall Molecule
DescriptionOctane is an alkane with the chemical formula C8H18. It has 18 isomers. One of the isomers, 2,2,4-trimethylpentane or isooctane, is of major importance, as it has been selected as the 100 point on the octane rating scale, with n-heptane as the zero point. Octane ratings are ratings used to represent the anti-knock performance of petroleum-based fuels (octane is less likely to prematurely combust under pressure than heptane), given as the percentage of 2,2,4-trimethylpentane in an 2,2,4-trimethylpentane / n-heptane mixture that would have the same performance. It is an important constituent of gasoline.
Compound Type
  • Food Toxin
  • Gasoline Additive/Component
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
N-Octane
Chemical FormulaC8H18
Average Molecular Mass114.229 g/mol
Monoisotopic Mass114.141 g/mol
CAS Registry Number111-65-9
IUPAC Nameoctane
Traditional Nameoctane
SMILESCCCCCCCC
InChI IdentifierInChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3
InChI KeyInChIKey=TVMXDCGIABBOFY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentAlkanes
Alternative ParentsNot Available
Substituents
  • Acyclic alkane
  • Alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-56.8°C
Boiling Point125.6°C (258.1°F)
Solubility0.00066 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogP5.18
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP4.73ALOGPS
logP4.02ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.61 m³·mol⁻¹ChemAxon
Polarizability16.42 ųChemAxon
Number of Rings0ChemAxon
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)splash10-052o-9000000000-dff2329c36bee36d9e672017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8dd19c0387246b61990c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-d2e1916d68421b9156162017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-08fr-9600000000-0ad297c5bbdcd8255dfc2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052o-9000000000-dff2329c36bee36d9e672018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8dd19c0387246b61990c2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-d2e1916d68421b9156162018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-08fr-9600000000-0ad297c5bbdcd8255dfc2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9100000000-734169bf6be23396487a2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-9200000000-7fa018b6e4635a5516212012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05mo-9000000000-ad7800923a7f89ae82a72012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aru-9100000000-a5dddfe6f629d1371fac2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052o-9000000000-dff2329c36bee36d9e672012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-8dd19c0387246b61990c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-0f2c1fefb3562ddd291c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positivesplash10-08fr-9600000000-0ad297c5bbdcd8255dfc2012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-3d7f12397b129744ef332017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-c56ee324b0ebcfc751e72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-fdc491d96317782d74122017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-eaa7ee0ef9699808e7002017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-486b5b971ea4d9a97ecb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9600000000-9ddf08fb6c571b873cbe2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9100000000-c3e1fce5b7d3e8c85d1a2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-6a868d2187f17076cbf62021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8fc55807287b28c39f952021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-e85376f8875d5d8518a42021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-7f4fa004fea60c3d18b72021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9500000000-7ccbab85bd6d6023347e2021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-6a16a91b5d23781341162014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 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 (15) ; inhalation (15) ; dermal (15)
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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesOctanes may be found in gasoline. (13)
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, 14)
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 IDDB02440
HMDB IDHMDB01485
PubChem Compound ID356
ChEMBL IDCHEMBL134886
ChemSpider ID349
KEGG IDC01387
UniProt IDNot Available
OMIM ID
ChEBI ID17590
BioCyc IDCPD-148
CTD IDNot Available
Stitch IDn-Octane
PDB IDOCT
ACToR ID3555
Wikipedia LinkOctane
References
Synthesis ReferenceNot Available
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. Kiso Y: Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study. Biofactors. 2004;21(1-4):191-6. [15630196 ]
  4. Claes C, Zivojnovic R: The use of perfluorocarbon liquids in vitreous surgery. Bull Soc Belge Ophtalmol. 1990;238:145-50. [2131117 ]
  5. Kramer KE, Andrews AR: Screening method for 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using hollow fiber membrane solvent microextraction with in-tube derivatization. J Chromatogr B Biomed Sci Appl. 2001 Aug 25;760(1):27-36. [11522063 ]
  6. Ivanova M, Piunti A, Marziali E, Komarova N, Raggi MA, Kenndler E: Microemulsion electrokinetic chromatography applied for separation of levetiracetam from other antiepileptic drugs in polypharmacy. Electrophoresis. 2003 Mar;24(6):992-8. [12658687 ]
  7. Le Mer Y, Haut J: [Use of perfluoro-octane liquid in the treatment of giant tears with inversion of the retina: preliminary results]. J Fr Ophtalmol. 1990;13(5):247-51. [2258547 ]
  8. Watzer B, Reinalter S, Seyberth HW, Schweer H: Determination of free and glucuronide conjugated 20-hydroxyarachidonic acid (20-HETE) in urine by gas chromatography/negative ion chemical ionization mass spectrometry. Prostaglandins Leukot Essent Fatty Acids. 2000 Mar;62(3):175-81. [10841040 ]
  9. Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. [8207942 ]
  10. Stone WL: Hydrophobic interaction of alkanes with liposomes and lipoproteins. J Biol Chem. 1975 Jun 10;250(11):4368-70. [165199 ]
  11. Dreisbach, RH (1983). Handbook of Poisoning. Los Altos, California: Lange Medical Publications.
  12. 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.
  13. Wikipedia. Octane. Last Updated 10 July 2009. [Link]
  14. 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]
  15. Wikipedia. Lead telluride. Last Updated 8 May 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. cAMP-dependent protein kinase catalytic subunit alpha
General Function:
Ubiquitin protein ligase binding
Specific Function:
Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which binds and ubiquitinates these subunits, leading to their subsequent proteolysis. Phosphorylates CDC25B, ABL1, NFKB1, CLDN3, PSMC5/RPT6, PJA2, RYR2, RORA and VASP. RORA is activated by phosphorylation. Required for glucose-mediated adipogenic differentiation increase and osteogenic differentiation inhibition from osteoblasts. Involved in the regulation of platelets in response to thrombin and collagen; maintains circulating platelets in a resting state by phosphorylating proteins in numerous platelet inhibitory pathways when in complex with NF-kappa-B (NFKB1 and NFKB2) and I-kappa-B-alpha (NFKBIA), but thrombin and collagen disrupt these complexes and free active PRKACA stimulates platelets and leads to platelet aggregation by phosphorylating VASP. Prevents the antiproliferative and anti-invasive effects of alpha-difluoromethylornithine in breast cancer cells when activated. RYR2 channel activity is potentiated by phosphorylation in presence of luminal Ca(2+), leading to reduced amplitude and increased frequency of store overload-induced Ca(2+) release (SOICR) characterized by an increased rate of Ca(2+) release and propagation velocity of spontaneous Ca(2+) waves, despite reduced wave amplitude and resting cytosolic Ca(2+). PSMC5/RPT6 activation by phosphorylation stimulates proteasome. Negatively regulates tight junctions (TJs) in ovarian cancer cells via CLDN3 phosphorylation. NFKB1 phosphorylation promotes NF-kappa-B p50-p50 DNA binding. Involved in embryonic development by down-regulating the Hedgehog (Hh) signaling pathway that determines embryo pattern formation and morphogenesis. Prevents meiosis resumption in prophase-arrested oocytes via CDC25B inactivation by phosphorylation. May also regulate rapid eye movement (REM) sleep in the pedunculopontine tegmental (PPT). Phosphorylates APOBEC3G and AICDA. Isoform 2 phosphorylates and activates ABL1 in sperm flagellum to promote spermatozoa capacitation.
Gene Name:
PRKACA
Uniprot ID:
P17612
Molecular Weight:
40589.38 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 ]
Target Details
2. 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. 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 ]