Guggulsterone (CHEM035466)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:47:23 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035466
Identification
Common NameGuggulsterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(8XI,9xi,14xi,17E)-20-methoxypregna-4,17-diene-3,16-dioneHMDB
20-Methoxy-4,17(20)e-pregnadiene-3,16-dioneHMDB
4,17(20)-Pregnadiene-3,16-dioneHMDB
Guggulsterone-mHMDB
Chemical FormulaC22H30O3
Average Molecular Mass342.472 g/mol
Monoisotopic Mass342.219 g/mol
CAS Registry Number95975-55-6
IUPAC Name(1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione
Traditional Name(Z)-guggulsterone
SMILES[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1
InChI KeyWOVLRQSWILBDQL-IABMEBKLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 16-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP3.5ALOGPS
logP3.46ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity100.48 m³·mol⁻¹ChemAxon
Polarizability39.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0200-0459000000-ee86b2088f6ad3cdf31dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1039000000-952388fe83cbda93ea21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ov-1279000000-5728b5f9167d8cb78890Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9083000000-b8990378d7107ffa738dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0029000000-5338c79160c73600c4b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0069000000-32d9482c72cfc85099ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-2090000000-69c0d68769a4ff1f7ec6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-91e1f5ec96b7e91e6084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-0089000000-b763db8304fe27efa3a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001u-0090000000-a41631240a8cd7b56409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-2538c557c24fab48c6bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r7-1389000000-a0a95688ed26bb666896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9430000000-3ba9301f7512c0faae5cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002726
FooDB IDFDB023055
Phenol Explorer IDNot Available
KNApSAcK IDC00047241
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGuggulsterone
Chemspider ID558777
ChEBI IDNot Available
PubChem Compound ID643658
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Khanna D, Sethi G, Ahn KS, Pandey MK, Kunnumakkara AB, Sung B, Aggarwal A, Aggarwal BB: Natural products as a gold mine for arthritis treatment. Curr Opin Pharmacol. 2007 Jun;7(3):344-51. Epub 2007 May 1.
2. Shishodia S, Aggarwal BB: Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis. J Biol Chem. 2004 Nov 5;279(45):47148-58. Epub 2004 Aug 17.