Showing Compound Card for campest-5-en-3β-ol-7-one (CDB000286)

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Record Information
Version1.0
Created at2020-03-19 00:28:57 UTC
Updated at2020-11-18 16:35:00 UTC
CannabisDB IDCDB000286
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecampest-5-en-3β-ol-7-one
DescriptionCampest-5-en-3β-ol-7-one or Campest-5-en-3beta-ol-7-one is an oxidized derivative of Campesterol (Campest-5-en-3-beta-ol) that has C=O double bond on the C-7 carbon. Campest-5-en-3β-ol-7-one is a neutral, hydrophobic molecule that is insoluble in water. Campest-5-en-3β-ol-7-one is a phytosterol, meaning it is a 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. 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. Phytosterols play a similar role to cholesterol in stabilizing membrane lipids in plants. 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. Campest-5-en-3β-ol-7-one is one of the several phytosterols found in the roots and leaves of cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC28H46O2
Average Molecular Weight414.67
Monoisotopic Molecular Weight414.3498
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-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,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-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)[C@H](C)CC[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
InChI Identifier
InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h16-19,21-24,26,29H,7-15H2,1-6H3/t18-,19-,21+,22-,23+,24+,26+,27+,28-/m1/s1
InChI KeyLTLKHSBYMNKWPF-KANLMKGOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-oxosteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP5.82ALOGPS
logP6.84ChemAxon
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
Refractivity125.81 m³·mol⁻¹ChemAxon
Polarizability52.59 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-MScampest-5-en-3β-ol-7-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScampest-5-en-3β-ol-7-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScampest-5-en-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 ID107449110
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101704474
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]