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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:02 UTC
HMDB IDHMDB0001217
Secondary Accession Numbers
  • HMDB0006926
  • HMDB01217
  • HMDB06926
Metabolite Identification
Common Name4alpha-Methylzymosterol
Description4alpha-Methylzymosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4alpha-methylzymosterol is considered to be a sterol lipid molecule. 4alpha-Methylzymosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4alpha-methylzymosterol has been detected, but not quantified in, several different foods, such as redcurrants, sunflowers, robusta coffees, white mustards, and sesbania flowers. This could make 4alpha-methylzymosterol a potential biomarker for the consumption of these foods. 4alpha-Methylzymosterol is an intermediate in the biosynthesis of steroids. It is the seventh to last step in the synthesis of vitamin D2 and is converted from 3-keto-4-methylzymosterol via the enzyme 3-keto steroid reductase (EC 1.1.1.270). It is then converted into zymosterol.
Structure
Data?1589403065
Synonyms
ValueSource
(3beta,4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-olChEBI
4alpha-Methyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b,4a,5a)-4-Methylcholesta-8,24-dien-3-olGenerator
(3β,4α,5α)-4-Methylcholesta-8,24-dien-3-olGenerator
4a-Methyl-5a-cholesta-8,24-dien-3b-olGenerator
4α-Methyl-5α-cholesta-8,24-dien-3β-olGenerator
(4S,5S)-4,10,13-Trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
4alpha-MethylzymosterolHMDB
4alpha-Methyl-5alpha-cholesta-8(9),24-dien-3beta-olHMDB
4alpha-Methyl-delta8,24-cholestenolHMDB
4α-Methyl-5α-cholesta-8(9),24-dien-3β-olHMDB
4α-Methyl-Δ8,24-cholestenolHMDB
4α-MethylzymosterolHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(2S,5S,6S,7S,11R,14R,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-ol
Traditional Name(2S,5S,6S,7S,11R,14R,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-ol
CAS Registry Number7448-03-5
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C28H46O/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/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1
InChI KeyFOUJWBXBKVVHCJ-YIJYGBTNSA-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-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP10(6.52) g/LALOGPS
logP10(7.03) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.67 m³·mol⁻¹ChemAxon
Polarizability51.73 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]+200.86431661259
DarkChem[M-H]-194.77131661259
AllCCS[M+H]+206.99432859911
AllCCS[M-H]-207.37632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4alpha-Methylzymosterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C2589.7Standard polar33892256
4alpha-Methylzymosterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C3206.3Standard non polar33892256
4alpha-Methylzymosterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C3206.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4alpha-Methylzymosterol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C)[C@@H]1CC33232.8Semi standard non polar33892256
4alpha-Methylzymosterol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1CC33463.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylzymosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ar-0019000000-da364020d6f55a8d18362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylzymosterol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3004900000-86ae2efd8b737e6752702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylzymosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-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 - 4alpha-Methylzymosterol 10V, Positive-QTOFsplash10-001j-0009000000-f485cbb263f2f4b1b84a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 20V, Positive-QTOFsplash10-01sj-2129000000-22c00d60920d1e5a4fab2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 40V, Positive-QTOFsplash10-014i-3459000000-7d25553141c326b6521e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 10V, Negative-QTOFsplash10-0002-0009000000-da18f5394671385950ba2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 20V, Negative-QTOFsplash10-0002-0009000000-dbaa936472d9a3662d912016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 40V, Negative-QTOFsplash10-0159-1009000000-dcd434b2beb43e39f10b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 20V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 40V, Negative-QTOFsplash10-0002-0009000000-4d79474ae6f15f5ccfe92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 10V, Positive-QTOFsplash10-000t-0019000000-7f62fafcf8fff91b75e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 20V, Positive-QTOFsplash10-066r-7279000000-1d2e823ffd821f5bcb5e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylzymosterol 40V, Positive-QTOFsplash10-0a4i-8940000000-81f109206bc11ddf7c5d2021-09-23Wishart 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 IDFDB022496
KNApSAcK IDNot Available
Chemspider ID20036827
KEGG Compound IDC05103
BioCyc ID4-METHYL-824-CHOLESTADIENOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280360
PDB IDNot Available
ChEBI ID1949
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 References
  1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

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