Showing Compound Card for 4a-Methylzymosterol (CDB005342)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 19:33:36 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005342
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4a-Methylzymosterol
Description4a-Methylzymosterol, also known as dinoproston or (15S)-prostaglandin E2, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4a-methylzymosterol is considered to be a sterol lipid molecule. 4a-Methylzymosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4a-Methylzymosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-olChEBI
4alpha-Methyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b,4a,5a)-4-Methylcholesta-8,24-dien-3-olGenerator
(3β,4α,5α)-4-Methylcholesta-8,24-dien-3-olGenerator
4a-Methyl-5a-cholesta-8,24-dien-3b-olGenerator
4α-Methyl-5α-cholesta-8,24-dien-3β-olGenerator
(4S,5S)-4,10,13-Trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
4alpha-MethylzymosterolHMDB
4alpha-Methyl-5alpha-cholesta-8(9),24-dien-3beta-olHMDB
4alpha-Methyl-delta8,24-cholestenolHMDB
4α-Methyl-5α-cholesta-8(9),24-dien-3β-olHMDB
4α-Methyl-Δ8,24-cholestenolHMDB
4α-MethylzymosterolHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.66
Monoisotopic Molecular Weight398.3549
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 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
CAS Registry Number7448-03-5
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=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
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

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.52ALOGPS
logP7.03ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.67 m³·mol⁻¹ChemAxon
Polarizability51.73 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-MS4a-Methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02ar-0019000000-da364020d6f55a8d1836Spectrum
Predicted GC-MS4a-Methylzymosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-3004900000-86ae2efd8b737e675270Spectrum
Predicted GC-MS4a-Methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4a-Methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-f485cbb263f2f4b1b84a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sj-2129000000-22c00d60920d1e5a4fab2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3459000000-7d25553141c326b6521e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-da18f5394671385950ba2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dbaa936472d9a3662d912016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-dcd434b2beb43e39f10b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-4d79474ae6f15f5ccfe92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0019000000-7f62fafcf8fff91b75e02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7279000000-1d2e823ffd821f5bcb5e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8940000000-81f109206bc11ddf7c5d2021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
3-keto-steroid reductaseHSD17B71q23P56937 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001217
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022496
KNApSAcK IDNot Available
Chemspider ID20036827
KEGG Compound IDC05103
BioCyc ID4-METHYL-824-CHOLESTADIENOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280360
PDB IDNot Available
ChEBI ID1949
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. 3-keto-steroid reductase
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77