Showing metabocard for Cholestenone (BMDB0000921)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:39 UTC
Update Date2020-05-11 20:38:18 UTC
BMDB IDBMDB0000921
Secondary Accession Numbers
  • BMDB00921
Metabolite Identification
Common NameCholestenone
DescriptionCholestenone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholestenone is considered to be a sterol. Based on a literature review a significant number of articles have been published on Cholestenone.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Cholesten-3-oneChEBI
Cholest-4-en-3-oneHMDB
(17b)-17-Octylandrost-4-en-3-oneHMDB
3-Oxocholest-4-eneHMDB
D4-Cholesten-3-oneHMDB
D4-CholestenoneHMDB
(+)-4-Cholesten-3-oneHMDB
(17beta)-17-Octylandrost-4-en-3-oneHMDB
(17Β)-17-octylandrost-4-en-3-oneHMDB
4-CholestenoneHMDB
CholesteroneHMDB
delta4-Cholesten-3-oneHMDB
delta4-CholestenoneHMDB
Δ4-cholesten-3-oneHMDB
Δ4-cholestenoneHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number601-57-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H44O/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/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyNYOXRYYXRWJDKP-GYKMGIIDSA-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
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point79 - 82 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.57ALOGPS
logP7.68ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.57 m³·mol⁻¹ChemAxon
Polarizability49.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-2229000000-cfc561b8bff8d7587819View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-3ba0c0c4f5b64032e969View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001j-9803000000-0041fa800c684344d6f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0532-9400000000-d0d60fb4fbca5c06cb01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-3ad74b36fc9e3f4b9db4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-b5cc0e7902cd6cdf783dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9700000000-d3906eae7c45c97a5b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-1fd5e37ad61a39390fabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9800000000-0f1c723e5ac58579caf8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9700000000-f5034b023ae3ba1d9577View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-6f526ead547a001ecc55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-3119000000-2a830558981b265c89c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-5239000000-c531237dfc518c04a8a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-fe5ea0c4be8b4b64ece7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-5d059b2d1fa5085dd8b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-2019000000-53be05d0d2e2dca6edfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-79017ac8303e5bbe2a84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-200e1637ea1dc1324da1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-060c-8269000000-6ca50c6965cc22bd1da8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-568f77aab2459f79ab93View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Gallbladder
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000921
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022319
KNApSAcK IDC00036093
Chemspider ID82602
KEGG Compound IDC00599
BioCyc IDCPD-323
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3898
PubChem Compound91477
PDB IDNot Available
ChEBI ID16175
References
Synthesis ReferenceMori, Susumu. Steroids. IX. A new synthesis of cholestenone and the addition of hypochlorous acid to cholesterol. Nippon Kagaku Kaishi (1921-47) (1952), Pure Chem. Sect. 73 547-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available