Hmdb loader
Survey
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 Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000871
Secondary Accession Numbers
  • HMDB00871
Metabolite Identification
Common Name5alpha-Cholestanone
Description5alpha-Cholestanone, also known as 5α-cholestanone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanone is considered to be a sterol lipid molecule. 5alpha-Cholestanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752161
Synonyms
ValueSource
5a-CholestanoneGenerator
5Α-cholestanoneGenerator
(5a,17b)-17-Octylandrostan-3-oneHMDB
(5alpha)-Cholestan-3-oneHMDB
(5alpha)-CholestanoneHMDB
5a(H)-Cholestan-3-oneHMDB
5a-Cholestan-3-oneHMDB
5alpha-Cholestane-3-oneHMDB
5alpha-CoprostanoneHMDB
Coprostanone, (5alpha)-isomerHMDB
Coprostanone, (5beta)-isomerHMDB
CoprostanoneHMDB
5-alpha-Cholestan-3-oneHMDB
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number566-88-1
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyPESKGJQREUXSRR-UXIWKSIVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point128 - 130 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.4e-05 g/LALOGPS
logP6.65ALOGPS
logP7.73ChemAxon
logS-7.4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.74 m³·mol⁻¹ChemAxon
Polarizability50.39 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]+196.14931661259
DarkChem[M-H]-193.88831661259
AllCCS[M+H]+203.63732859911
AllCCS[M-H]-202.84532859911
DeepCCS[M-2H]-234.1130932474
DeepCCS[M+Na]+208.11230932474
AllCCS[M+H]+203.632859911
AllCCS[M+H-H2O]+201.532859911
AllCCS[M+NH4]+205.632859911
AllCCS[M+Na]+206.232859911
AllCCS[M-H]-202.832859911
AllCCS[M+Na-2H]-204.632859911
AllCCS[M+HCOO]-206.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Cholestanone[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C2671.9Standard polar33892256
5alpha-Cholestanone[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3124.8Standard non polar33892256
5alpha-Cholestanone[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3195.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Cholestanone,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3121.6Semi standard non polar33892256
5alpha-Cholestanone,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3061.9Standard non polar33892256
5alpha-Cholestanone,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3418.5Standard polar33892256
5alpha-Cholestanone,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3100.6Semi standard non polar33892256
5alpha-Cholestanone,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3113.9Standard non polar33892256
5alpha-Cholestanone,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3416.7Standard polar33892256
5alpha-Cholestanone,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3357.0Semi standard non polar33892256
5alpha-Cholestanone,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3234.0Standard non polar33892256
5alpha-Cholestanone,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3539.6Standard polar33892256
5alpha-Cholestanone,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3337.0Semi standard non polar33892256
5alpha-Cholestanone,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3291.4Standard non polar33892256
5alpha-Cholestanone,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3540.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanone GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-1e285528ee9f0b57935d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanone GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-6bb813789665ec6a16282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanone GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-1e285528ee9f0b57935d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanone GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-6bb813789665ec6a16282018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1119000000-9809fd6827c971c15cbd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0009000000-4d86603e7a3a04181d6b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9700000000-ab5536500bf3ce457af02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05nf-9400000000-df0bf747717b6f9029972012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 10V, Positive-QTOFsplash10-000i-0009000000-d67fc5e4a90e5d444b4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 20V, Positive-QTOFsplash10-0avr-3109000000-6cb93905134a4bd15b662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 40V, Positive-QTOFsplash10-0abc-4129000000-9147166fdcb0a41b5fb92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 10V, Negative-QTOFsplash10-000i-0009000000-dc54e67e8b668159df032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 20V, Negative-QTOFsplash10-000i-0009000000-e72d372e493f1796a5722017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 40V, Negative-QTOFsplash10-066u-2019000000-49f63f8ed5d9e7e3d6732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 10V, Negative-QTOFsplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 20V, Negative-QTOFsplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 40V, Negative-QTOFsplash10-001i-0009000000-0799374e96775b3163db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 10V, Positive-QTOFsplash10-000i-0009000000-85d8a5bf63fedb0c361c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 20V, Positive-QTOFsplash10-06dj-9164000000-a2efdb351bfe2dea81fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanone 40V, Positive-QTOFsplash10-052f-9710000000-de7ec5cb56f34f7b69c52021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart 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 IDFDB022292
KNApSAcK IDNot Available
Chemspider ID83174
KEGG Compound IDC03238
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5832
PubChem Compound92128
PDB IDNot Available
ChEBI ID17762
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCargill, D. I. The separation of cholesterol from related stanols and stanones by thin-layer chromatography. Analyst (1962), 87 865-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. McNamara DJ, Proia A, Miettinen TA: Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. J Lipid Res. 1981 Mar;22(3):474-84. [PubMed:7240972 ]
  2. Strandberg TE, Tilvis RS, Miettinen TA: Metabolic variables of cholesterol during squalene feeding in humans: comparison with cholestyramine treatment. J Lipid Res. 1990 Sep;31(9):1637-43. [PubMed:2246614 ]
  3. Reddy BS, Wynder EL: Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer. 1977 Jun;39(6):2533-9. [PubMed:872053 ]