Showing Compound Card for Zymosterol intermediate 2 (CDB005343)

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Record Information
Version1.0
Created at2020-04-17 19:33:42 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005343
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameZymosterol intermediate 2
DescriptionZymosterol intermediate 2, also known as zymostrol or 5a-cholesta-8,24-dien-3b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Zymosterol intermediate 2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Zymosterol intermediate 2 is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5alpha-Cholesta-8,24-dien-3beta-olChEBI
delta8,24-Cholestadien-3beta-olChEBI
ZymostrolChEBI
5a-Cholesta-8,24-dien-3b-olGenerator
5Α-cholesta-8,24-dien-3β-olGenerator
delta8,24-Cholestadien-3b-olGenerator
Δ8,24-cholestadien-3β-olGenerator
Zymosterol intermediic acid 2Generator
Δ8,24-cholestadien-3b-olHMDB
(3b,5a)- Cholesta-8,24-dien-3-olHMDB
Cholest-8,24-dien-3b-olHMDB
Cholesta-8,24-dien-3-olHMDB
ZymosterolHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.64
Monoisotopic Molecular Weight384.3392
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
Traditional 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
CAS Registry Number128-33-6
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
InChI Identifier
InChI=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
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 Point110 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
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 IDHMDB0006271
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031258
KNApSAcK IDC00023749
Chemspider ID83724
KEGG Compound IDC05437
BioCyc IDNot Available
BiGG ID1454806
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92746
PDB IDNot Available
ChEBI ID18252
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