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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-16 15:27:12 UTC
HMDB IDHMDB0000941
Secondary Accession Numbers
  • HMDB00941
Metabolite Identification
Common NameCholest-5-ene
DescriptionCholest-5-ene, also known as 5-cholestene, belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. Thus, cholest-5-ene is considered to be a sterol. Based on a literature review a significant number of articles have been published on Cholest-5-ene.
Structure
Data?1582752166
Synonyms
ValueSource
5-CholesteneChEBI
D5-CholesteneHMDB
Cholest-5-eneKEGG
Chemical FormulaC27H46
Average Molecular Weight370.6541
Monoisotopic Molecular Weight370.359951472
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene
Traditional Namecholest-5-ene
CAS Registry Number570-74-1
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C
InChI Identifier
InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h12,19-20,22-25H,6-11,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyDTGDZMYNKLTSKC-HKQCOZBKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholestane steroids
Alternative Parents
Substituents
  • Cholestane-skeleton
  • Delta-5-steroid
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
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 Solubility1.2e-05 g/LALOGPS
logP10(7.87) g/LALOGPS
logP10(8.5) g/LChemAxon
logS10(-7.5) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.95 m³·mol⁻¹ChemAxon
Polarizability49.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.31231661259
DarkChem[M-H]-189.0131661259
AllCCS[M+H]+200.20432859911
AllCCS[M-H]-201.22432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cholest-5-ene[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C2883.9Standard polar33892256
Cholest-5-ene[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C2925.0Standard non polar33892256
Cholest-5-ene[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C2832.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-1229000000-e2078e492439a3aca82c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 10V, Positive-QTOFsplash10-00di-1119000000-64abbbde0fdcbb52f7632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 20V, Positive-QTOFsplash10-05i0-5269000000-4cab5e10f9179e6512092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 40V, Positive-QTOFsplash10-0a4i-8469000000-cb62741b93259b6ad9d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 10V, Negative-QTOFsplash10-014i-0009000000-f8995c6171def5ad35302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 20V, Negative-QTOFsplash10-014i-0009000000-6b9f58cc842b53f3a65a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 40V, Negative-QTOFsplash10-0udr-2139000000-74d55a222821b15f13ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 10V, Positive-QTOFsplash10-00di-0009000000-333124946ccb2f9590f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 20V, Positive-QTOFsplash10-05fr-9462000000-307fdd169d0e31c025a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 40V, Positive-QTOFsplash10-0aba-9430000000-fef5cdb755a2fa7fac792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 10V, Negative-QTOFsplash10-014i-0009000000-e97c1bb5837bea46af052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 20V, Negative-QTOFsplash10-014i-0009000000-e97c1bb5837bea46af052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene 40V, Negative-QTOFsplash10-014i-0019000000-8fb2f12d17039ddc8e0b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022329
KNApSAcK IDC00046564
Chemspider ID389543
KEGG Compound IDC05416
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5889
PubChem Compound440663
PDB IDNot Available
ChEBI ID28810
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBaker, Robert H.; Squire, Edward N. Derived steroids. I. Cholesteryl ketones. Journal of the American Chemical Society (1948), 70 1487-90.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Waters JA: Photosensitized isomerization-hydration of 5-cholestene. Steroids. 1974 Feb;23(2):259-67. [PubMed:4818028 ]
  2. Swell L, Gustafsson J, Schwartz CC, Halloran LG, Danielsson H, Vlahcevic ZR: An in vivo evaluation of the quantitative significance of several potential pathways to cholic and chenodeoxycholic acids from cholesterol in man. J Lipid Res. 1980 May;21(4):455-66. [PubMed:7381336 ]
  3. Bjorkhem I, Andersson U, Ellis E, Alvelius G, Ellegard L, Diczfalusy U, Sjovall J, Einarsson C: From brain to bile. Evidence that conjugation and omega-hydroxylation are important for elimination of 24S-hydroxycholesterol (cerebrosterol) in humans. J Biol Chem. 2001 Oct 5;276(40):37004-10. Epub 2001 Jul 19. [PubMed:11463788 ]
  4. Esfahani M, Scerbo L, Devlin TM: A requirement for cholesterol and its structural features for a human macrophage-like cell line. J Cell Biochem. 1984;25(2):87-97. [PubMed:6480716 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325