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
Molecular FormulaC28H46O
Average Mass398.66420
Monoisotopic Mass398.35487
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 Name4α-methylzymosterol
CAS Registry Number7448-03-05
SMILESCC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@@H]1CC3
InChI IdentifierInChI=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
CHEBI IDCHEBI:1949
HMDB IDHMDB0001217
Pathways
NameSMPDB/PathBank
Steroid Biosynthesis
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Atorvastatin Action Pathway
Hypercholesterolemia
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
StateSolid
Water Solubility7.04e-04 g/l
logP6.52
logS-5.75
pKa (Strongest Acidic)18.96
pKa (Strongest Basic)-1.07
Hydrogen Acceptor Count1
Hydrogen Donor Count1
Polar Surface Area20.23 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity125.67 m³·mol⁻¹
Polarizability51.58

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