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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:36:12 UTC
Update Date2022-03-07 03:17:38 UTC
HMDB IDHMDB0059909
Secondary Accession Numbers
  • HMDB59909
Metabolite Identification
Common NameEicosane
DescriptionEicosane, also known as CH3-[CH2]18-CH3 or octyldodecane, 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. Eicosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, eicosane is considered to be a hydrocarbon lipid molecule. Eicosane is an alkane and waxy tasting compound. Eicosane is found, on average, in the highest concentration within lemon balms. Eicosane has also been detected, but not quantified, in several different foods, such as allspices, papaya, coconuts, lindens, and hyssops. This could make eicosane a potential biomarker for the consumption of these foods. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2.
Structure
Data?1563865990
Synonyms
ValueSource
CH3-[CH2]18-CH3ChEBI
N-EicosaneChEBI
OctyldodecaneChEBI
IcosaneHMDB
EicosaneChEBI
Chemical FormulaC20H42
Average Molecular Weight282.5475
Monoisotopic Molecular Weight282.328651344
IUPAC Nameicosane
Traditional Nameeicosane
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
InChI KeyCBFCDTFDPHXCNY-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
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.9e-06 g/LALOGPS
logP9.78ALOGPS
logP9.36ChemAxon
logS-7.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity93.82 m³·mol⁻¹ChemAxon
Polarizability41.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.61831661259
DarkChem[M-H]-177.79931661259
DeepCCS[M+H]+174.46930932474
DeepCCS[M-H]-171.2830932474
DeepCCS[M-2H]-207.96830932474
DeepCCS[M+Na]+183.63530932474
AllCCS[M+H]+190.532859911
AllCCS[M+H-H2O]+187.632859911
AllCCS[M+NH4]+193.132859911
AllCCS[M+Na]+193.932859911
AllCCS[M-H]-182.532859911
AllCCS[M+Na-2H]-184.132859911
AllCCS[M+HCOO]-186.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EicosaneCCCCCCCCCCCCCCCCCCCC2013.0Standard polar33892256
EicosaneCCCCCCCCCCCCCCCCCCCC2001.6Standard non polar33892256
EicosaneCCCCCCCCCCCCCCCCCCCC2003.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Eicosane GC-MS (Non-derivatized)splash10-00dr-9200000000-8803c91354a1f4960a852014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eicosane EI-B (Non-derivatized)splash10-0a4l-9000000000-e134070d5bd2cd5dee702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eicosane EI-B (Non-derivatized)splash10-0a4l-9000000000-1fd25ca00429cf4bd43d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eicosane CI-B (Non-derivatized)splash10-001i-0190000000-81b5d2ec93cf739de33d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eicosane GC-MS (Non-derivatized)splash10-00dr-9200000000-8803c91354a1f4960a852017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eicosane GC-MS (Non-derivatized) - 70eV, Positivesplash10-01oy-7930000000-a5a9b082673eeafa59fd2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eicosane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0abc-9100000000-b92ea993ede560d3e2642015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 10V, Positive-QTOFsplash10-001i-0090000000-ef9266b4b096cf893a462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 20V, Positive-QTOFsplash10-001i-4590000000-6f101d621da0fe5e73572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 40V, Positive-QTOFsplash10-052f-9330000000-f24eba03ec54f2f1d5042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 10V, Negative-QTOFsplash10-001i-0090000000-f01176d740a265b10e812016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 20V, Negative-QTOFsplash10-001i-0090000000-b6e5280c48745c65e5492016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 40V, Negative-QTOFsplash10-00lr-5980000000-7fff407e6bd02c2d99de2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 10V, Positive-QTOFsplash10-001i-2090000000-1b47e5bd0719b7ceb2e12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 20V, Positive-QTOFsplash10-0ac0-9040000000-54ad57abc7ff884306012021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 40V, Positive-QTOFsplash10-0a4l-9000000000-1ea9f51470b4a38df9442021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 10V, Negative-QTOFsplash10-001i-0090000000-d080e436874ff278c4b82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 20V, Negative-QTOFsplash10-001i-0090000000-d080e436874ff278c4b82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eicosane 40V, Negative-QTOFsplash10-001i-1290000000-07da13bfd390e992a4662021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004727
KNApSAcK IDNot Available
Chemspider ID7929
KEGG Compound IDNot Available
BioCyc IDCPD-14231
BiGG IDNot Available
Wikipedia LinkIcosane
METLIN IDNot Available
PubChem Compound8222
PDB IDLFA
ChEBI ID43619
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ma MT, Neels OC, Denoyer D, Roselt P, Karas JA, Scanlon DB, White JM, Hicks RJ, Donnelly PS: Gallium-68 complex of a macrobicyclic cage amine chelator tethered to two integrin-targeting peptides for diagnostic tumor imaging. Bioconjug Chem. 2011 Oct 19;22(10):2093-103. doi: 10.1021/bc200319q. Epub 2011 Sep 27. [PubMed:21877750 ]
  2. Aroulanda C, Zimmermann H, Luz Z, Lesot P: Enantiotopic discrimination in the deuterium NMR spectrum of solutes with S4 symmetry in chiral liquid crystals. J Chem Phys. 2011 Apr 7;134(13):134502. doi: 10.1063/1.3554640. [PubMed:21476759 ]
  3. Zhou S, Lee AK, McWhinney RD, Abbatt JP: Burial effects of organic coatings on the heterogeneous reactivity of particle-borne benzo[a]pyrene (BaP) toward ozone. J Phys Chem A. 2012 Jul 5;116(26):7050-6. doi: 10.1021/jp3030705. Epub 2012 Jun 21. [PubMed:22676584 ]
  4. Ma MT, Cooper MS, Paul RL, Shaw KP, Karas JA, Scanlon D, White JM, Blower PJ, Donnelly PS: Macrobicyclic cage amine ligands for copper radiopharmaceuticals: a single bivalent cage amine containing two Lys3-bombesin targeting peptides. Inorg Chem. 2011 Jul 18;50(14):6701-10. doi: 10.1021/ic200681s. Epub 2011 Jun 13. [PubMed:21667932 ]
  5. Rivera A, Quiroga D, Rios-Motta J, Fejfarova K, Dusek M: The disordered molecular structure of (3aRS,7aRS)-1,3-dinitrosooctahydro-1H-benzimidazole. Acta Crystallogr C. 2011 Dec;67(Pt 12):o505-8. doi: 10.1107/S0108270111046397. Epub 2011 Nov 22. [PubMed:22138925 ]
  6. Khani A, Asghari J: Insecticide activity of essential oils of Mentha longifolia, Pulicaria gnaphalodes and Achillea wilhelmsii against two stored product pests, the flour beetle, Tribolium castaneum, and the cowpea weevil, Callosobruchus maculatus. J Insect Sci. 2012;12:73. doi: 10.1673/031.012.7301. [PubMed:23413994 ]
  7. Yucel U, Elias RJ, Coupland JN: Solute distribution and stability in emulsion-based delivery systems: an EPR study. J Colloid Interface Sci. 2012 Jul 1;377(1):105-13. doi: 10.1016/j.jcis.2012.03.071. Epub 2012 Apr 1. [PubMed:22533996 ]
  8. Yucel U, Elias RJ, Coupland JN: Localization and reactivity of a hydrophobic solute in lecithin and caseinate stabilized solid lipid nanoparticles and nanoemulsions. J Colloid Interface Sci. 2013 Mar 15;394:20-5. doi: 10.1016/j.jcis.2012.12.042. Epub 2012 Dec 28. [PubMed:23352869 ]
  9. Rizwan K, Zubair M, Rasool N, Riaz M, Zia-Ul-Haq M, de Feo V: Phytochemical and biological studies of Agave attenuata. Int J Mol Sci. 2012;13(5):6440-51. doi: 10.3390/ijms13056440. Epub 2012 May 24. [PubMed:22754375 ]
  10. Cai H, Li Z, Huang CW, Park R, Shahinian AH, Conti PS: An improved synthesis and biological evaluation of a new cage-like bifunctional chelator, 4-((8-amino-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1-ylamino)methyl)benzoic acid, for 64Cu radiopharmaceuticals. Nucl Med Biol. 2010 Jan;37(1):57-65. doi: 10.1016/j.nucmedbio.2009.09.001. Epub 2009 Oct 12. [PubMed:20122669 ]
  11. Samori C, Guerrini A, Varchi G, Beretta GL, Fontana G, Bombardelli E, Carenini N, Zunino F, Bertucci C, Fiori J, Battaglia A: The role of polyamine architecture on the pharmacological activity of open lactone camptothecin-polyamine conjugates. Bioconjug Chem. 2008 Nov 19;19(11):2270-9. doi: 10.1021/bc800033r. [PubMed:18839979 ]
  12. Avendano C, Lafitte T, Adjiman CS, Galindo A, Muller EA, Jackson G: SAFT-gamma force field for the simulation of molecular fluids: 2. Coarse-grained models of greenhouse gases, refrigerants, and long alkanes. J Phys Chem B. 2013 Mar 7;117(9):2717-33. doi: 10.1021/jp306442b. Epub 2013 Feb 27. [PubMed:23311931 ]
  13. Brown KN, Geue RJ, Hambley TW, Hockless DC, Rae AD, Sargeson AM: Specificity in template syntheses of hexaaza-macrobicyclic cages: [Pt(Me5-tricosatrieneN6)]4+ and [Pt(Me5-tricosaneN6)]4+. Org Biomol Chem. 2003 May 7;1(9):1598-608. [PubMed:12926293 ]
  14. Cai H, Li Z, Huang CW, Shahinian AH, Wang H, Park R, Conti PS: Evaluation of copper-64 labeled AmBaSar conjugated cyclic RGD peptide for improved microPET imaging of integrin alphavbeta3 expression. Bioconjug Chem. 2010 Aug 18;21(8):1417-24. doi: 10.1021/bc900537f. [PubMed:20666401 ]
  15. Sen Gupta N, Wragg DS, Tilset M, Omtvedt JP: 4,7,13,18-Tetra-oxa-1,10-diazo-nia-bicyclo-[8.5.5]icosane hexa-fluorido-silicate. Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):o1958-9. doi: 10.1107/S1600536811026006. Epub 2011 Jul 9. [PubMed:22090998 ]
  16. Baatour O, Tarchoune I, Mahmoudi H, Nassri N, Abidi W, Kaddour R, Hamdaoui G, Nasri-Ayachi MB, Lachaal M, Marzouk B: Culture conditions and salt effects on essential oil composition of sweet marjoram (Origanum majorana) from Tunisia. Acta Pharm. 2012 Jun;62(2):251-61. doi: 10.2478/v10007-012-0019-9. [PubMed:22750822 ]
  17. Rockey WM, Huang L, Kloepping KC, Baumhover NJ, Giangrande PH, Schultz MK: Synthesis and radiolabeling of chelator-RNA aptamer bioconjugates with copper-64 for targeted molecular imaging. Bioorg Med Chem. 2011 Jul 1;19(13):4080-90. doi: 10.1016/j.bmc.2011.05.010. Epub 2011 May 14. [PubMed:21658962 ]
  18. Kostereli Z, Severin K: Fluorescence sensing of spermine with a frustrated amphiphile. Chem Commun (Camb). 2012 Jun 14;48(47):5841-3. doi: 10.1039/c2cc32228e. Epub 2012 May 9. [PubMed:22573305 ]
  19. Kadali KK, Simons KL, Skuza PP, Moore RB, Ball AS: A complementary approach to identifying and assessing the remediation potential of hydrocarbonoclastic bacteria. J Microbiol Methods. 2012 Mar;88(3):348-55. doi: 10.1016/j.mimet.2011.12.006. Epub 2012 Jan 5. [PubMed:22245375 ]
  20. Sen Gupta N, Wragg DS, Tilset M, Omtvedt JP: 4,7,13,18-Tetra-oxa-1,10-diazo-nia-bicyclo-[8.5.5]icosane bis-(hexa-fluorido-phosphate). Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):o1929-30. doi: 10.1107/S1600536811025992. Epub 2011 Jul 6. [PubMed:22090974 ]