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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 10:45:47 UTC
Update Date2021-09-14 15:07:03 UTC
HMDB IDHMDB0006838
Secondary Accession Numbers
  • HMDB0006923
  • HMDB06838
  • HMDB06923
Metabolite Identification
Common Name3-Keto-4-methylzymosterol
Description3-Keto-4-methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG:C15816). It is the 8th to last step in the synthesis of vitamin D2 and is converted from 4-methtylzymosterol-carboxylate via the enzyme sterol-4alpha-carboxylate 3-dehydrogenase (decarboxylating) (EC:1.1.1.170). It is then converted to 4-methylzymosterol via the enzyme 3-keto steroid reductase (EC:1.1.1.270).
Structure
Data?1582752409
Synonyms
ValueSource
(5a)-4-Methylcholesta-8,24-dien-3-oneHMDB
(5alpha)-4-Methylcholesta-8,24-dien-3-oneHMDB
3-Dehydro-4-methylzymosterolHMDB
4-Methyl-5a-cholesta-8,24-dien-3-oneHMDB
4-Methyl-5alpha-cholesta-8,24-dien-3-oneHMDB
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(2S,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
Traditional Name(2S,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
CAS Registry NumberNot Available
SMILES
C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3
InChI Identifier
InChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20?,22?,23?,24?,27-,28+/m1/s1
InChI KeyDBPZYKHQDWKORQ-JQDPPCHWSA-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

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00056 g/LALOGPS
logP10(7.22) g/LALOGPS
logP10(7.41) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity124.75 m³·mol⁻¹ChemAxon
Polarizability50.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.98231661259
DarkChem[M-H]-191.03931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Keto-4-methylzymosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-02au-2019000000-5173500b11e18ce35b3b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Keto-4-methylzymosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Keto-4-methylzymosterol 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 - 3-Keto-4-methylzymosterol 10V, Positive-QTOFsplash10-0002-0009000000-00d160bd3605d4c8b8462016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 20V, Positive-QTOFsplash10-00pv-1119000000-e5a9171fb6049ee634312016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 40V, Positive-QTOFsplash10-015i-2119000000-6b021eb86e51393d97982016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 10V, Negative-QTOFsplash10-0002-0009000000-e91a27c7e4df70239c242016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 20V, Negative-QTOFsplash10-0002-0009000000-766b7ce92b3bc6de20e72016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 40V, Negative-QTOFsplash10-01t9-3009000000-b4ba7e91fae9c3e7a4ba2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 10V, Positive-QTOFsplash10-002b-0019000000-f87374bf70bdfa4a699f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 20V, Positive-QTOFsplash10-0ap0-3259000000-e97d8860c45e22b2a89d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 40V, Positive-QTOFsplash10-0a4i-6951000000-99c4649de525703330a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 10V, Negative-QTOFsplash10-0002-0009000000-2f6aa9af0bd8878fb6c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 20V, Negative-QTOFsplash10-0002-0009000000-2f6aa9af0bd8878fb6c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Keto-4-methylzymosterol 40V, Negative-QTOFsplash10-0007-0009000000-3e9131f464f27a3024a52021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024112
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15816
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477900
PDB IDNot Available
ChEBI ID505093
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
Reactions
4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol + NADP → 3-Keto-4-methylzymosterol + NADPH + Hydrogen Ion + Carbon dioxidedetails
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
Reactions
3-Keto-4-methylzymosterol + NADPH + Hydrogen Ion → 4alpha-Methylzymosterol + NADPdetails