Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 08:08:35 UTC
Update Date2021-09-24 08:08:35 UTC
HMDB IDHMDB0304222
Secondary Accession NumbersNone
Metabolite Identification
Common Name5alpha-cholesta-8,24-dien-3-one
Description5alpha-cholesta-8,24-dien-3-one, also known as zymosterone, belongs to cholesterols and derivatives class of compounds. Those are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholesta-8,24-dien-3-one is considered to be a sterol lipid molecule. 5alpha-cholesta-8,24-dien-3-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 5alpha-cholesta-8,24-dien-3-one can be found in a number of food items such as cloudberry, welsh onion, oil-seed camellia, and loquat, which makes 5alpha-cholesta-8,24-dien-3-one a potential biomarker for the consumption of these food products. 5alpha-cholesta-8,24-dien-3-one may be a unique S.cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
ValueSource
ZymosteroneChEBI
Chemical FormulaC27H42O
Average Molecular Weight382.6218
Monoisotopic Molecular Weight382.323565966
IUPAC Name(2S,7S,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 Name5α-cholesta-8,24-dien-3-one
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C[C@]1([H])CC3)[C@H](C)CCC=C(C)C
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-ZSBATXSLSA-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
  • 3-oxo-5-alpha-steroid
  • 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 Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
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
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
AllCCS[M+H]+202.8732859911
AllCCS[M+H-H2O]+200.63732859911
AllCCS[M+Na]+205.51532859911
AllCCS[M+NH4]+204.92632859911
AllCCS[M-H]-205.4332859911
AllCCS[M+Na-2H]-206.83132859911
AllCCS[M+HCOO]-208.53232859911
DeepCCS[M-2H]-237.53630932474
DeepCCS[M+Na]+212.23730932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-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)CCC(O[Si](C)(C)C)=C[C@@H]1CC33209.5Semi standard non polar33892256
5alpha-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)CCC(O[Si](C)(C)C)=C[C@@H]1CC33123.8Standard non polar33892256
5alpha-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)CCC(O[Si](C)(C)C)=C[C@@H]1CC33475.5Standard polar33892256
5alpha-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)CC=C(O[Si](C)(C)C)C[C@@H]1CC33212.4Semi standard non polar33892256
5alpha-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)CC=C(O[Si](C)(C)C)C[C@@H]1CC33074.7Standard non polar33892256
5alpha-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)CC=C(O[Si](C)(C)C)C[C@@H]1CC33478.1Standard polar33892256
5alpha-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)CCC(O[Si](C)(C)C(C)(C)C)=C[C@@H]1CC33442.4Semi standard non polar33892256
5alpha-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)CCC(O[Si](C)(C)C(C)(C)C)=C[C@@H]1CC33320.9Standard non polar33892256
5alpha-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)CCC(O[Si](C)(C)C(C)(C)C)=C[C@@H]1CC33599.9Standard polar33892256
5alpha-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)CC=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1CC33448.6Semi standard non polar33892256
5alpha-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)CC=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1CC33254.2Standard non polar33892256
5alpha-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)CC=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1CC33601.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 10V, Positive-QTOFsplash10-001i-0019000000-fafef18f6f1e438c21d02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 20V, Positive-QTOFsplash10-017i-1129000000-2006cfbeb2221efe12222016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 40V, Positive-QTOFsplash10-016r-4139000000-16eafffededcd9fa46002016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-06c184e2361b4ee6c5b42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-8b4140bf264b853e09fe2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 40V, Negative-QTOFsplash10-0gba-3019000000-d44463d2ecf3bc057e662016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 10V, Positive-QTOFsplash10-001i-0019000000-ad25e0dccfe72be6cb9e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 20V, Positive-QTOFsplash10-0l6r-6498000000-5090eda806a93a3004e32021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 40V, Positive-QTOFsplash10-052f-7941000000-4022ce530acf9ad2ea962021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 10V, Negative-QTOFsplash10-001i-0009000000-334e990fc728bf944c792021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 20V, Negative-QTOFsplash10-001i-0009000000-6abcbf0582c0df66e7192021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-cholesta-8,24-dien-3-one 40V, Negative-QTOFsplash10-004i-0009000000-75a25b37df692b4de81c2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB030588
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22298942
PDB IDNot Available
ChEBI ID52386
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