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zymosterol (FDB031258)

Record Information
Version1.0
Creation date2015-05-07 21:27:32 UTC
Update date2019-11-26 03:22:14 UTC
Primary IDFDB031258
Secondary Accession Numbers
  • FDB023869
Chemical Information
FooDB Namezymosterol
DescriptionZymosterol, also known as 5alpha-cholesta-8,24-dien-3beta-ol or delta8,24-cholestadien-3beta-ol, belongs to cholesterols and derivatives class of compounds. Those are compounds containing a 3-hydroxylated cholestane core. Thus, zymosterol is considered to be a sterol lipid molecule. Zymosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Zymosterol can be synthesized from 5alpha-cholestane. Zymosterol is also a parent compound for other transformation products, including but not limited to, 4beta-methylzymosterol-4alpha-carboxylic acid, 3-dehydro-4-methylzymosterol, and zymosterol intermediate 1b. Zymosterol can be found in a number of food items such as squashberry, hard wheat, salmonberry, and loquat, which makes zymosterol a potential biomarker for the consumption of these food products. Zymosterol exists in all eukaryotes, ranging from yeast to humans. In humans, zymosterol is involved in several metabolic pathways, some of which include zoledronate action pathway, alendronate action pathway, pravastatin action pathway, and atorvastatin action pathway. Zymosterol is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, lysosomal acid lipase deficiency (wolman disease), smith-lemli-opitz syndrome (SLOS), and chondrodysplasia punctata II, X linked dominant (CDPX2). Zymosterol is an intermediate in cholesterol biosynthesis. Disregarding some intermediate compounds (e.g. 4-4-dimethylzymosterol) lanosterol can be considered a precursor of zymosterol in the cholesterol synthesis pathway. The conversion of zymosterol into cholesterol happens in the endoplasmic reticulum. Zymosterol accumulates quickly in the plasma membrane coming from the cytosol. The movement of zymosterol across the cytosol is more than twice as fast as the movement of cholesterol itself .
CAS Number128-33-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP6.51ALOGPS
logP6.66ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.2 m³·mol⁻¹ChemAxon
Polarizability49.72 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H44O
IUPAC name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
InChI IdentifierInChI=1S/C27H44O/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/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChI KeyCGSJXLIKVBJVRY-XTGBIJOFSA-N
Isomeric SMILES[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
Classification
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:

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Process

Naturally occurring process:

Role

Biological role:

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSZymosterol intermediate 2, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0cfr-1019000000-1b05483747ddc32500b0Spectrum
Predicted GC-MSZymosterol intermediate 2, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-3106900000-eda3cfead337ce02b2b5Spectrum
Predicted GC-MSZymosterol intermediate 2, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSZymosterol intermediate 2, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-010b245dedfb160716ba2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2149000000-c0828080ef844c1d5c692016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vi-3259000000-96993d821222323ab0752016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-0373115d11504acc8b812016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-cc742e0af833cc290a8f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-1019000000-87e4aab6501a99f5baec2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0019000000-384e7aa03192295e15892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-3fe44ab0178bb12e2a162021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4249000000-ee1fd80800f89af74a912021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-8930000000-32bc5a989db5c704eabf2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference