Showing Compound Card for 5a-Cholest-8-en-3b-ol (CDB005344)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2)transporters (1) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:33:48 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005344
Secondary Accession NumbersNot Available
Cannabis Compound 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. 5a-Cholest-8-en-3b-ol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight386.65
Monoisotopic Molecular Weight386.3549
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5a-Cholest-8-en-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-076r-1019000000-da210f056bd723d532a1Spectrum
Predicted GC-MS5a-Cholest-8-en-3b-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-3105900000-25f7266fb84218fbea74Spectrum
Predicted GC-MS5a-Cholest-8-en-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-a776f0a6c0141e92ae732017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3139000000-e84343d3954ffbe258f22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-5b6b7a2f03b59d0933252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-315c5133aa81b39394742017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-711bf432a79ce66b987f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1019000000-b4dfc241017aaa46ed222017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-04cb77df44ddc15c479c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0009000000-41e086d5b3ca90d0da912021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0609-9345000000-80072d6556dbb8a419e12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-8950000000-c4785344c8ab4e1aea5c2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006841
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Enzyme Details
2. Delta(24)-sterol reductase
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805

Transporters

Enzyme Details
1. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615