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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001093
Secondary Accession Numbers
  • HMDB01093
Metabolite Identification
Common Name5a-Cholesta-8,24-dien-3-one
Description5a-Cholesta-8,24-dien-3-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 5a-Cholesta-8,24-dien-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752176
Synonyms
ValueSource
5alpha-Cholesta-8,24-dien-3-oneHMDB
Chemical FormulaC27H42O
Average Molecular Weight382.6218
Monoisotopic Molecular Weight382.323565966
IUPAC Name(2S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one
Traditional Name5a-cholesta-8,24-dien-3-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=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/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20?,23-,24+,26+,27-/m1/s1
InChI KeyAUNLIRXIJAVBNM-YBXLEUBGSA-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
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00071 g/LALOGPS
logP6.92ALOGPS
logP6.87ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.17 m³·mol⁻¹ChemAxon
Polarizability48.85 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]+194.46431661259
DarkChem[M-H]-191.16431661259
AllCCS[M+H]+202.93432859911
AllCCS[M-H]-205.4332859911
DeepCCS[M-2H]-230.51630932474
DeepCCS[M+Na]+205.69330932474
AllCCS[M+H]+202.932859911
AllCCS[M+H-H2O]+200.732859911
AllCCS[M+NH4]+205.032859911
AllCCS[M+Na]+205.632859911
AllCCS[M-H]-205.432859911
AllCCS[M+Na-2H]-206.832859911
AllCCS[M+HCOO]-208.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5a-Cholesta-8,24-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=O)CC[C@]12C2979.5Standard polar33892256
5a-Cholesta-8,24-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=O)CC[C@]12C3081.6Standard non polar33892256
5a-Cholesta-8,24-dien-3-one[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=O)CC[C@]12C3180.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC33224.0Semi standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC33080.5Standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1CC33468.1Standard polar33892256
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC33227.4Semi standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC33135.2Standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1CC33466.3Standard polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC33458.5Semi standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC33264.2Standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1CC33590.5Standard polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC33460.4Semi standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC33337.0Standard non polar33892256
5a-Cholesta-8,24-dien-3-one,1TBDMS,isomer #2CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1CC33589.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5a-Cholesta-8,24-dien-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0j4i-1129000000-82f247afa5987b19470a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5a-Cholesta-8,24-dien-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5a-Cholesta-8,24-dien-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 10V, Positive-QTOFsplash10-001i-0019000000-eeeda54c958f4f8019342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 20V, Positive-QTOFsplash10-069r-2019000000-4594055189900f888c412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 40V, Positive-QTOFsplash10-0a4i-2119000000-f91042fa1f198d0309982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-7b4e3a203e59d7ab5dcc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-fa4b37050bbe0b9886312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 40V, Negative-QTOFsplash10-0gb9-2019000000-fadfaff0ff3fdfb82b3d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 10V, Positive-QTOFsplash10-001i-0019000000-067d9efd4b46723383892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 20V, Positive-QTOFsplash10-0gi3-5279000000-e0d6750c533d10f9e6702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 40V, Positive-QTOFsplash10-052f-8943000000-a9e0a0a61251d66e5c1c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-334e990fc728bf944c792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-4fc2fb75ab62f8c34d432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Cholesta-8,24-dien-3-one 40V, Negative-QTOFsplash10-00o0-1149000000-18c7c7cd3f7331490dcb2021-09-24Wishart 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 IDFDB022422
KNApSAcK IDNot Available
Chemspider ID17216058
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5999
PubChem Compound22833560
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
Not Available
Gene Name:
NSDHL
Uniprot ID:
Q15738
Molecular weight:
41899.99
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77