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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:54:25 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0061782
Secondary Accession Numbers
  • HMDB61782
Metabolite Identification
Common NameHeneicosane
DescriptionHeneicosane, also known as CH3-[CH2]19-CH3, 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. Thus, heneicosane is considered to be a hydrocarbon lipid molecule. Heneicosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heneicosane is an alkane and waxy tasting compound. Heneicosane is found, on average, in the highest concentration within a few different foods, such as black elderberries, common oregano, and lemon balms. Heneicosane has also been detected, but not quantified, in several different foods, such as sunflowers, kohlrabis, orange bell peppers, lindens, and pepper (c. annuum). This could make heneicosane a potential biomarker for the consumption of these foods. An alkane that has 21 carbons and a straight-chain structure.
Structure
Data?1563866230
Synonyms
ValueSource
CH3-[CH2]19-CH3ChEBI
N-HeneicosaneChEBI
HeneicosaneChEBI
Chemical FormulaC21H44
Average Molecular Weight296.5741
Monoisotopic Molecular Weight296.344301408
IUPAC Namehenicosane
Traditional Nameheneicosane
CAS Registry Number629-94-7
SMILES
CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3
InChI KeyFNAZRRHPUDJQCJ-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
Role
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 Solubility6.1e-06 g/LALOGPS
logP9.98ALOGPS
logP9.8ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity98.42 m³·mol⁻¹ChemAxon
Polarizability44.09 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]+180.51731661259
DarkChem[M-H]-181.74631661259
DeepCCS[M+H]+179.1330932474
DeepCCS[M-H]-175.39830932474
DeepCCS[M-2H]-212.44630932474
DeepCCS[M+Na]+188.21830932474
AllCCS[M+H]+195.632859911
AllCCS[M+H-H2O]+192.832859911
AllCCS[M+NH4]+198.132859911
AllCCS[M+Na]+198.932859911
AllCCS[M-H]-185.932859911
AllCCS[M+Na-2H]-187.632859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HeneicosaneCCCCCCCCCCCCCCCCCCCCC2111.4Standard polar33892256
HeneicosaneCCCCCCCCCCCCCCCCCCCCC2102.8Standard non polar33892256
HeneicosaneCCCCCCCCCCCCCCCCCCCCC2104.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Heneicosane GC-MS (Non-derivatized)splash10-00dr-9200000000-2dd012b1c9f68451dee42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heneicosane EI-B (Non-derivatized)splash10-0a4l-9000000000-e59f7d9328ef554ce2842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heneicosane EI-B (Non-derivatized)splash10-0a4l-9100000000-2bc507df938a82e990b12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heneicosane CI-B (Non-derivatized)splash10-0002-1290000000-b4e97f1d11340cd3d2352017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosane GC-MS (Non-derivatized) - 70eV, Positivesplash10-01oy-7940000000-cd1476e8593aee6b136e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0abc-9100000000-3e6355dfa6070f094f0c2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 10V, Positive-QTOFsplash10-0002-0090000000-20296a7137ca1b281e952016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 20V, Positive-QTOFsplash10-0002-3490000000-5234ed80f1cff8786d2a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 40V, Positive-QTOFsplash10-0006-9550000000-f0a08f3520804320f3ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 10V, Negative-QTOFsplash10-0002-0090000000-81c5362622d211d7aa862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 20V, Negative-QTOFsplash10-0002-0090000000-99bb69c15db09959e7df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 40V, Negative-QTOFsplash10-002b-6690000000-3386a1085d6dcbfff9c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 10V, Positive-QTOFsplash10-0002-2090000000-a4bbb7da3437da5d756b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 20V, Positive-QTOFsplash10-0592-9040000000-51434738299870ca1a832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 40V, Positive-QTOFsplash10-0a4l-9000000000-2c74ba35d964f4254bb22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 10V, Negative-QTOFsplash10-0002-0090000000-4f5b7d0ce45cf76fc3f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 20V, Negative-QTOFsplash10-0002-0090000000-4f5b7d0ce45cf76fc3f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosane 40V, Negative-QTOFsplash10-0002-1190000000-ea859877fa7fc6f27bfa2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDFDB004728
KNApSAcK IDNot Available
Chemspider ID11897
KEGG Compound IDNot Available
BioCyc IDCPD-7935
BiGG IDNot Available
Wikipedia LinkHigher alkanes
METLIN IDNot Available
PubChem Compound12403
PDB IDNot Available
ChEBI ID32931
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. Brown GO, Guardala NA, Price JL, Weiss RG: Selectivity and efficiency of pyrene attachment to alkanes induced by broadband X-rays. An Acad Bras Cienc. 2003 Mar;75(1):33-8. Epub 2003 Apr 17. [PubMed:12715048 ]
  2. Yang XM, Fu EQ: [Synthesis and spectral characterization of novel chiral macrocyclic dioxopolyamines]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jul;27(7):1403-7. [PubMed:17944424 ]
  3. Seenivasagan T, Sharma KR, Sekhar K, Ganesan K, Prakash S, Vijayaraghavan R: Electroantennogram, flight orientation, and oviposition responses of Aedes aegypti to the oviposition pheromone n-heneicosane. Parasitol Res. 2009 Mar;104(4):827-33. doi: 10.1007/s00436-008-1263-2. Epub 2008 Nov 19. [PubMed:19018567 ]
  4. Yu AN, Sun BG, Hu WB: Top note compounds of Chinese traditional bacteria-fermented soybean. Nat Prod Res. 2008;22(17):1552-9. doi: 10.1080/14786410701824791. [PubMed:19023819 ]
  5. Li G, Dhinojwala A, Yeganeh MS: Interfacial structure and melting temperature of alcohol and alkane molecules in contact with polystyrene films. J Phys Chem B. 2009 Mar 5;113(9):2739-47. doi: 10.1021/jp8065663. [PubMed:19708209 ]
  6. Bhutia YD, Gautam A, Jain N, Ahmed F, Sharma M, Singh R, Kumar S, Mendki MJ, Kumar P, Vijayaraghavan R: Acute and sub-acute toxicity of an insect pheromone, N-heneicosane and combination with insect growth regulator, diflubenzuron, for establishing no observed adverse effect level (NOAEL). Indian J Exp Biol. 2010 Jul;48(7):744-51. [PubMed:20929058 ]
  7. Wikipedia [Link]
  8. Shri Prakash et al. 'Composition for Use in Controlling Aedes Aegypti Mosquitoes.' U.S. Patent US20080274076, issued November 06, 2008. [Link]
  9. Kumaran Ganesan, Ramesh Chandra Malhotra, Ambati Narasimha Rao, Krishnamurthy Sekhar, 'Process for the Preparation of N-Heneicosane.' U.S. Patent US20080293992, issued November 27, 2008. [Link]
  10. Kumaran Ganesan, Ramesh Chandra Malhotra, Ambati Narasimha Rao, Pradeep Kumar Gupta, Asheesh Kumar Jain, Shri Prakash, Krishnamurthy Sekhar, 'Process for the preparation of n-heneicosane.' U.S. Patent US07615672, issued November 10, 2009. [Link]