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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:57 UTC
Update Date2022-03-07 02:53:01 UTC
HMDB IDHMDB0031542
Secondary Accession Numbers
  • HMDB31542
Metabolite Identification
Common NameMethylcyclopentane
DescriptionMethylcyclopentane, also known as methylpentamethylene, belongs to the class of organic compounds known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains). Methylcyclopentane has been detected, but not quantified, in celeriacs and celery stalks. This could make methylcyclopentane a potential biomarker for the consumption of these foods. At high amounts methylcyclopentane is a potentially toxic compound and central nervous system depression may occur, with symptoms such as weakness, dizziness, slow and shallow respiration, unconsciousness, and convulsions. Methylcyclopentane is a volatile component of petroleum distillates. Petroleum 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. Volatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. Treatment is mainly symptomatic and supportive. Petroleum distillates are also irritating to the skin. Petroleum distillate poisoning may cause nausea, vomiting, cough, pulmonary irritation progressing to pulmonary edema, bloody sputum, and bronchial pneumonia. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration.
Structure
Data?1563862138
Synonyms
ValueSource
Methyl cyclopentaneChEBI
Methyl-cyclopentaneChEBI
MethylpentamethyleneChEBI
Chemical FormulaC6H12
Average Molecular Weight84.1595
Monoisotopic Molecular Weight84.093900384
IUPAC Namemethylcyclopentane
Traditional Namemethylcyclopentane
CAS Registry Number96-37-7
SMILES
CC1CCCC1
InChI Identifier
InChI=1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3
InChI KeyGDOPTJXRTPNYNR-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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-139.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.37Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP3.15ALOGPS
logP2.51ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.55 m³·mol⁻¹ChemAxon
Polarizability11.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+116.38331661259
DarkChem[M-H]-109.73431661259
DeepCCS[M+H]+126.64330932474
DeepCCS[M-H]-124.64530932474
DeepCCS[M-2H]-160.07630932474
DeepCCS[M+Na]+134.59930932474
AllCCS[M+H]+116.732859911
AllCCS[M+H-H2O]+111.632859911
AllCCS[M+NH4]+121.532859911
AllCCS[M+Na]+122.932859911
AllCCS[M-H]-124.132859911
AllCCS[M+Na-2H]-127.932859911
AllCCS[M+HCOO]-132.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylcyclopentaneCC1CCCC1694.9Standard polar33892256
MethylcyclopentaneCC1CCCC1612.3Standard non polar33892256
MethylcyclopentaneCC1CCCC1627.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methylcyclopentane EI-B (Non-derivatized)splash10-0a4l-9000000000-f36947d92a09565016ad2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylcyclopentane CI-B (Non-derivatized)splash10-001i-9000000000-89652fbd27509594b6192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylcyclopentane EI-B (Non-derivatized)splash10-0a4l-9000000000-f36947d92a09565016ad2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylcyclopentane CI-B (Non-derivatized)splash10-001i-9000000000-89652fbd27509594b6192018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylcyclopentane GC-MS (Non-derivatized) - 70eV, Positivesplash10-069u-9000000000-f20228dae0dda76bc5672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylcyclopentane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-e94ad8098b4b70c9d7482014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 10V, Positive-QTOFsplash10-000i-9000000000-32d4c2667ea3fb16d0df2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 20V, Positive-QTOFsplash10-000i-9000000000-d818a8aa9bf254dadac52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 40V, Positive-QTOFsplash10-0a4l-9000000000-df6a147e653036178f262015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 10V, Negative-QTOFsplash10-001i-9000000000-6d1754df5318b34cabe22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 20V, Negative-QTOFsplash10-001i-9000000000-6d1754df5318b34cabe22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 40V, Negative-QTOFsplash10-00lr-9000000000-f8ed5bb4f934bc89073f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 10V, Positive-QTOFsplash10-0a4r-9000000000-79a23acab097b8c24d752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 20V, Positive-QTOFsplash10-0a4l-9000000000-deb6f40b714e47a3d1322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 40V, Positive-QTOFsplash10-0006-9000000000-87fe95b8405e28cf90fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 10V, Negative-QTOFsplash10-001i-9000000000-1fe2685b7f3004ca04a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 20V, Negative-QTOFsplash10-001i-9000000000-386a19febdb8857d4e222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylcyclopentane 40V, Negative-QTOFsplash10-001i-9000000000-bea98e26b5e568f762382021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDFDB008152
KNApSAcK IDNot Available
Chemspider ID7024
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylcyclopentane
METLIN IDNot Available
PubChem Compound7296
PDB IDNot Available
ChEBI ID88429
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
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  9. Wu Z, Lifka J, Ondruschka B: Benzene formation during aquasonolysis of selected cyclic C6Hx hydrocarbons. Ultrason Sonochem. 2005 Jan;12(1-2):133-6. [PubMed:15474966 ]
  10. Zhang L, Feng L, Jia Q, Xu J, Wang R, Wang Z, Wu Y, Li Y: Effects of beta-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro. Bioorg Med Chem. 2011 Aug 15;19(16):4882-6. doi: 10.1016/j.bmc.2011.06.069. Epub 2011 Jun 29. [PubMed:21775152 ]
  11. Zimniak A: Electron ionization-induced fragmentation of R2N2Fe2(CO)6 complexes with distinct geometries of the tetrahedral core: investigation of mu-1,2-(1,2-diaza-3-methylcyclopentane)diylbis(tricarbonyliron) and bis(mu2-acetophenoniminato)bis(tricarbonyliron). J Mass Spectrom. 2002 Nov;37(11):1145-51. [PubMed:12447891 ]
  12. Lee JW, Lu H, Moudrakovski IL, Ratcliffe CI, Ohmura R, Alavi S, Ripmeester JA: 13C NMR studies of hydrocarbon guests in synthetic structure H gas hydrates: experiment and computation. J Phys Chem A. 2011 Mar 10;115(9):1650-7. doi: 10.1021/jp1118184. Epub 2011 Feb 17. [PubMed:21329330 ]
  13. Sari O, Roy V, Balzarini J, Snoeck R, Andrei G, Agrofoglio LA: Synthesis and antiviral evaluation of C5-substituted-(1,3-diyne)-2'-deoxyuridines. Eur J Med Chem. 2012 Jul;53:220-8. doi: 10.1016/j.ejmech.2012.04.001. Epub 2012 Apr 21. [PubMed:22578783 ]
  14. Moustafa NE: Gas chromatographic analysis of petroleum associated condensate oil with simultaneous determination of some characteristic physical parameters. J Chromatogr Sci. 2008 May-Jun;46(5):388-91. [PubMed:18492346 ]
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