You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP7.87ALOGPS
logP8.5ChemAxon
logS-7.5ALOGPS
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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available193.31231661259
DarkChem[M-H]-PredictedNot Available189.0131661259
AllCCS[M+H]+PredictedNot Available200.20432859911
AllCCS[M-H]-PredictedNot Available201.22432859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-1229000000-e2078e492439a3aca82c2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1119000000-64abbbde0fdcbb52f7632017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-5269000000-4cab5e10f9179e6512092017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8469000000-cb62741b93259b6ad9d82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-f8995c6171def5ad35302017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-6b9f58cc842b53f3a65a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-2139000000-74d55a222821b15f13ab2017-09-01View 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
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