Showing metabocard for 5a-Cholest-8-en-3b-ol (BMDB0006841)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:40 UTC
Update Date2020-05-21 16:27:03 UTC
BMDB IDBMDB0006841
Secondary Accession Numbers
  • BMDB06841
Metabolite Identification
Common Name5a-Cholest-8-en-3b-ol
Description​5alpha-Cholest-8-en-3beta-ol, also known as cholestenol or zymostenol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, ​5alpha-cholest-8-en-3beta-ol is considered to be a sterol lipid molecule. ​5alpha-Cholest-8-en-3beta-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CholestenolChEBI
ZymostenolChEBI
​5a-cholest-8-en-3b-olGenerator
​5α-cholest-8-en-3β-olGenerator
(3beta,5alpha)CholestenolHMDB
3beta-Hydroxy-8(9)-cholesteneHMDB
3beta-Hydroxycholest-8(9)-eneHMDB
5-alpha-Cholest-8-en-3-beta-olHMDB
5alpha-Cholest-8(9)-en-3beta-olHMDB
5alpha-Cholest-8-en-3beta-olHMDB
Cholest-8(9)-en-3beta-olHMDB
Cholesta-8(9)-en-3beta-olHMDB
delta(8)-CholestenolHMDB
8(9)-CholestenolHMDB
Zymostenol, (3beta)-isomerHMDB
(3beta,5alpha)-Cholest-8-en-3-olHMDB
(3Β,5α)-cholest-8-en-3-olHMDB
3beta-Hydroxy-5alpha-cholest-8(9)-eneHMDB
3Β-hydroxy-5α-cholest-8(9)-eneHMDB
5a-Cholest-8-en-3b-olHMDB
5Α-cholest-8-en-3β-olHMDB
DihydrozymosterolHMDB
delta8-CholestenolHMDB
Δ8-cholestenolHMDB
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number566-97-2
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O/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/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChI KeyQETLKNDKQOXZRP-XTGBIJOFSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.59ALOGPS
logP7.07ChemAxon
logS-6.2ALOGPS
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 Count5ChemAxon
Refractivity120.35 m³·mol⁻¹ChemAxon
Polarizability50.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-1019000000-da210f056bd723d532a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3105900000-25f7266fb84218fbea74View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-a776f0a6c0141e92ae73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3139000000-e84343d3954ffbe258f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-5b6b7a2f03b59d093325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-315c5133aa81b3939474View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-711bf432a79ce66b987fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1019000000-b4dfc241017aaa46ed22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-04cb77df44ddc15c479cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0009000000-41e086d5b3ca90d0da91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0609-9345000000-80072d6556dbb8a419e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-8950000000-c4785344c8ab4e1aea5cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006841
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024114
KNApSAcK IDC00033775
Chemspider ID91952
KEGG Compound IDC03845
BioCyc IDCPD-8621
BiGG ID42633
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101770
PDB IDNot Available
ChEBI ID16608
References
Synthesis ReferenceReindel, F.; Weickmann, A. Zymosterol. Ann. (1929), 475 86-100. CAN 24:5322 AN 1930:5322
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. EBP cholestenol delta-isomerase
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Not Available
Gene Name:
EBP
Uniprot ID:
Q3ZBT8
Molecular weight:
26480.0
Reactions
Lathosterol → 5a-Cholest-8-en-3b-oldetails
Enzyme Details
2. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
Zymosterol intermediate 2 + NADPH → 5a-Cholest-8-en-3b-ol + NADPdetails