Showing Compound Card for Stigmasta-5,22-dien-3β-ol-7-one (CDB000288)

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Record Information
Version1.0
Created at2020-03-19 00:29:04 UTC
Updated at2020-11-18 16:35:00 UTC
CannabisDB IDCDB000288
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameStigmasta-5,22-dien-3β-ol-7-one
DescriptionStigmasta-5,22-dien-3β-ol-7-one is a derivative of stigmasterol (stigmasta-5,22-dien-3β-ol) that has C=O double bond positioned on the C-7 carbon. It belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. Stigmasta-5,22-dien-3β-ol-7-one is a neutral, hydrophobic molecule that is insoluble in water. It is a phytosterol, meaning it is steroid derived from plants. Phytosterols have a cholesterol-like structure consisting of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or the presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits (PMID: 28702423 ). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423 ). They may also have a role in cancer prevention and treatment (PMID: 26086253 ). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Stigmasta-5,22-dien-3β-ol-7-one is one of several phytosterols that are found in cannabis plants (https://doi.org/10.1007/978-1-59259-947-9_2), (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC29H46O2
Average Molecular Weight426.69
Monoisotopic Molecular Weight426.3498
IUPAC Name(1S,2R,5S,10R,11R,14R,15R)-14-[(2R,3Z,5R)-5-ethyl-6-methylhept-3-en-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one
Traditional Name(1S,2R,5S,10R,11R,14R,15R)-14-[(2R,3Z,5R)-5-ethyl-6-methylhept-3-en-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one
CAS Registry NumberNot Available
SMILES
CC[C@@H](\C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O)C(C)C
InChI Identifier
InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h8-9,17-20,22-25,27,30H,7,10-16H2,1-6H3/b9-8-/t19-,20+,22+,23-,24-,25+,27-,28+,29-/m1/s1
InChI KeyUKMCCFHULJHJNS-RBXNOROVSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.8ALOGPS
logP6.92ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)17.39ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.53 m³·mol⁻¹ChemAxon
Polarizability52.41 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-MSStigmasta-5,22-dien-3β-ol-7-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSStigmasta-5,22-dien-3β-ol-7-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSStigmasta-5,22-dien-3β-ol-7-one, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. [PubMed:28702423 ]
  2. Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. [PubMed:26086253 ]
  3. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]