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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2021-09-16 15:27:23 UTC
HMDB IDHMDB0002394
Secondary Accession Numbers
  • HMDB02394
Metabolite Identification
Common NameCholesta-4,6-dien-3-one
DescriptionCholesta-4,6-dien-3-one is a product of the oxidation of cholesteral. It may be metabolized to 4-cholesten-3-one and cholestanol by liver, adrenals and brain. An accumulation of cholesta-4,6-dien-3-one is found in serum of patients with cerebrotendinous xanthomatosis, and it is possible that accumulation of cholesterol in these patients is secondary to accumulation of cholesta-4,6-dien-3-one (PMID: 3557306 ; 16757819; 3676336).
Structure
Data?1582752248
Synonyms
ValueSource
4,6-Cholestadien-3-oneHMDB, MeSH
4,6-Cholestadiene-3-oneHMDB
Cholest-4,6-dien-3-oneMeSH, HMDB
Cholesta-4,6-diene-3-oneMeSH, HMDB
Chemical FormulaC27H42O
Average Molecular Weight382.6218
Monoisotopic Molecular Weight382.323565966
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]heptadeca-6,8-dien-5-one
Traditional Namecholesta-4,6-dien-3-one
CAS Registry Number566-93-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C27H42O/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/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyXIWMRKFKSRYSIJ-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
  • 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
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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available208.318http://allccs.zhulab.cn/database/detail?ID=AllCCS00001242
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP10(6.31) g/LALOGPS
logP10(7.32) g/LChemAxon
logS10(-7.2) g/LALOGPS
pKa (Strongest Acidic)19.94ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.68 m³·mol⁻¹ChemAxon
Polarizability49.21 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]+194.58831661259
DarkChem[M-H]-192.51631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cholesta-4,6-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C3740.6Standard polar33892256
Cholesta-4,6-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C3168.6Standard non polar33892256
Cholesta-4,6-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C3300.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cholesta-4,6-dien-3-one,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3235.1Semi standard non polar33892256
Cholesta-4,6-dien-3-one,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3197.3Standard non polar33892256
Cholesta-4,6-dien-3-one,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3504.7Standard polar33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3476.4Semi standard non polar33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3386.4Standard non polar33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3642.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cholesta-4,6-dien-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-2239000000-553c810e1d19e3831e2b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholesta-4,6-dien-3-one 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 - Cholesta-4,6-dien-3-one 40V, Positive-QTOFsplash10-0bt9-0900000000-75bf77729496522672822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOFsplash10-001i-0519000000-d3546c4987360df326ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOFsplash10-001i-0009000000-17d134ad7478d2eabf412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOFsplash10-001i-0019000000-976c7ec9b4ecd0f35ce12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOFsplash10-0api-3119000000-4c6c7aa38dc7223607b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Positive-QTOFsplash10-0a4i-6239000000-e36074a482541cfecb972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-ab162bbf77e93fdedda92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-8854ae94fc792ba973a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Negative-QTOFsplash10-0gba-2019000000-166d4a573bdfe5e551252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOFsplash10-001i-0009000000-dcbeb6d0adb3f19621462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOFsplash10-066r-6594000000-093e658315d31d30c0c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Positive-QTOFsplash10-0ab9-3921000000-1fa63eae5ed59c0d90412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-334e990fc728bf944c792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-334e990fc728bf944c792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Negative-QTOFsplash10-001i-0049000000-c2d8d78e4aa615befe082021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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 IDFDB022993
KNApSAcK IDNot Available
Chemspider ID2299095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6663
PubChem Compound3034666
PDB IDNot Available
ChEBI ID205734
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceParish, Edward J.; Sun, Hang; Lu, Ding; Kizito, Stephen A.; Qiu, Zhihai. New chemical syntheses of cholest-4,6-dien-3-one. Lipids (2002), 37(12), 1197-1200.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Buchmann MS, Bjorkhem I, Skrede S: Metabolism of the cholestanol precursor cholesta-4,6-dien-3-one in different tissues. Biochim Biophys Acta. 1987 Nov 21;922(2):111-7. [PubMed:3676336 ]
  2. Bjorkhem I, Skrede S, Buchmann MS, East C, Grundy S: Accumulation of 7 alpha-hydroxy-4-cholesten-3-one and cholesta-4,6-dien-3-one in patients with cerebrotendinous xanthomatosis: effect of treatment with chenodeoxycholic acid. Hepatology. 1987 Mar-Apr;7(2):266-71. [PubMed:3557306 ]
  3. Liu ZQ, Shan HY: Cholesterol, not polyunsaturated fatty acids, is target molecule in oxidation induced by reactive oxygen species in membrane of human erythrocytes. Cell Biochem Biophys. 2006;45(2):185-93. [PubMed:16757819 ]