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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-13 20:51:05 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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name4α-methylzymosterol
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP6.52ALOGPS
logP7.03ChemAxon
logS-5.8ALOGPS
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
Polarizability51.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ar-0019000000-da364020d6f55a8d1836Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3004900000-86ae2efd8b737e675270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-f485cbb263f2f4b1b84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sj-2129000000-22c00d60920d1e5a4fabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3459000000-7d25553141c326b6521eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-da18f5394671385950baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dbaa936472d9a3662d91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-dcd434b2beb43e39f10bSpectrum
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 ID
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