Cholestenone (CHEM034996)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:18 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034996
Identification
Common NameCholestenone
ClassSmall Molecule
DescriptionA cholestanoid that is cholest-4-ene substituted by an oxo group at position 3.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass384.638 g/mol
Monoisotopic Mass384.339 g/mol
CAS Registry Number601-57-0
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
SMILES[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-2229000000-cfc561b8bff8d7587819Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-3ba0c0c4f5b64032e969Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001j-9803000000-0041fa800c684344d6f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0532-9400000000-d0d60fb4fbca5c06cb01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-3ad74b36fc9e3f4b9db4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-b5cc0e7902cd6cdf783dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9700000000-d3906eae7c45c97a5b78Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7900000000-1fd5e37ad61a39390fabSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9800000000-0f1c723e5ac58579caf8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4j-9700000000-f5034b023ae3ba1d9577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-6f526ead547a001ecc55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-3119000000-2a830558981b265c89c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-5239000000-c531237dfc518c04a8a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-fe5ea0c4be8b4b64ece7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-5d059b2d1fa5085dd8b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-2019000000-53be05d0d2e2dca6edfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-79017ac8303e5bbe2a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-200e1637ea1dc1324da1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-060c-8269000000-6ca50c6965cc22bd1da8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-568f77aab2459f79ab93Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000921
FooDB IDFDB022319
Phenol Explorer IDNot Available
KNApSAcK IDC00036093
BiGG IDNot Available
BioCyc IDCPD-323
METLIN ID3898
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82602
ChEBI ID16175
PubChem Compound ID91477
Kegg Compound IDC00599
YMDB IDNot Available
ECMDB IDM2MDB004823
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10566877
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11958788
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12036855
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12777473
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12943786
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14597406
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17496168
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20671299
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24465993
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24565079
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24927729
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29201491
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29413944
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29573289
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31477154
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6892636
17. Mori, 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.
18. Nguyen DH, Taub D: Cholesterol is essential for macrophage inflammatory protein 1 beta binding and conformational integrity of CC chemokine receptor 5. Blood. 2002 Jun 15;99(12):4298-306.
19. Nguyen DH, Taub DD: Inhibition of chemokine receptor function by membrane cholesterol oxidation. Exp Cell Res. 2003 Nov 15;291(1):36-45.
20. Norlin M, von Bahr S, Bjorkhem I, Wikvall K: On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation. J Lipid Res. 2003 Aug;44(8):1515-22. Epub 2003 Jun 1.
21. Maeda Y, Kamimura R, Higashi S, Namba K, Tanaka E, Iwamura T, Setoguchi T: A simple, accurate, and sensitive assay method of dehydroepiandrosterone sulfate: application for quantitative determination in human breast cyst and duct fluids. Steroids. 2002 Apr;67(5):333-8.
22. Weststrate JA, Ayesh R, Bauer-Plank C, Drewitt PN: Safety evaluation of phytosterol esters. Part 4. Faecal concentrations of bile acids and neutral sterols in healthy normolipidaemic volunteers consuming a controlled diet either with or without a phytosterol ester-enriched margarine. Food Chem Toxicol. 1999 Nov;37(11):1063-71.
23. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.