Record Information
Version1.0
Creation date2011-09-21 00:22:58 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB022993
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number566-93-8
Structure
Thumb
Synonyms
SynonymSource
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
cholesta-4,6-dien-3-onehmdb
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP6.31ALOGPS
logP7.32ChemAxon
logS-7.2ALOGPS
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
Chemical FormulaC27H42O
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight382.6218
Monoisotopic Molecular Weight382.323565966
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCholesta-4,6-dien-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-2239000000-553c810e1d19e3831e2bSpectrum
Predicted GC-MSCholesta-4,6-dien-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0900000000-75bf7772949652267282Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0519000000-d3546c4987360df326abSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-17d134ad7478d2eabf41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-976c7ec9b4ecd0f35ce1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-3119000000-4c6c7aa38dc7223607b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6239000000-e36074a482541cfecb97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-ab162bbf77e93fdedda9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-8854ae94fc792ba973a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gba-2019000000-166d4a573bdfe5e55125Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-dcbeb6d0adb3f1962146Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-6594000000-093e658315d31d30c0c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-3921000000-1fa63eae5ed59c0d9041Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-334e990fc728bf944c79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-334e990fc728bf944c79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0049000000-c2d8d78e4aa615befe08Spectrum
NMRNot Available
ChemSpider ID2299095
ChEMBL IDCHEMBL68121
KEGG Compound IDNot Available
Pubchem Compound ID3034666
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02394
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference