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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:06 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002726
Secondary Accession Numbers
  • HMDB02726
Metabolite Identification
Common NameGuggulsterone
DescriptionGuggulsterone is an ingredient in many nutritional supplements. Guggulsterone is a plant sterol derived from the gum resin (guggulu) of the tree Commiphora mukul. This sterol can inhibit NF-κB activation and downregulate the expression of inflammatory gene products such as COX-2 and MMP-9, which are major players in the development of arthritis. Guggulsterone also can suppress osteoclastogenesis induced by RANKL (receptor activator of NF-κB ligand), a bone-resorbing cytokine. The anti-inflammatory activity of C. mukul (guggul) has been compared with that of NSAIDs, namely phenylbutazone and ibuprofen. Guggulsterone is used to treat obesity, diabetes, hyperlipidemia, atherosclerosis, and osteoarthritis, and has been recently shown to antagonize the farnesoid X receptor and decrease the expression of bile acid-activated genes. It modulates activation of NF-kappaB, which has been closely linked with inflammatory diseases affected by guggulsterone. (PMID: 17475558 , 15322087 ).
Structure
Data?1582752255
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 Weight342.4718
Monoisotopic Molecular Weight342.219494826
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
CAS Registry Number95975-55-6
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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.75 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-217.85830932474
DeepCCS[M+Na]+193.80630932474
AllCCS[M+H]+185.832859911
AllCCS[M+H-H2O]+183.132859911
AllCCS[M+NH4]+188.432859911
AllCCS[M+Na]+189.132859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-192.332859911
AllCCS[M+HCOO]-193.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Guggulsterone[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C3781.5Standard polar33892256
Guggulsterone[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C2749.2Standard non polar33892256
Guggulsterone[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C3024.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guggulsterone,1TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C3029.4Semi standard non polar33892256
Guggulsterone,1TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C2730.5Standard non polar33892256
Guggulsterone,1TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C3315.5Standard polar33892256
Guggulsterone,1TMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C2972.9Semi standard non polar33892256
Guggulsterone,1TMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C2787.4Standard non polar33892256
Guggulsterone,1TMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3312.6Standard polar33892256
Guggulsterone,2TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C2950.2Semi standard non polar33892256
Guggulsterone,2TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C2839.5Standard non polar33892256
Guggulsterone,2TMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3343.2Standard polar33892256
Guggulsterone,1TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C3260.4Semi standard non polar33892256
Guggulsterone,1TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C2934.4Standard non polar33892256
Guggulsterone,1TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C3452.6Standard polar33892256
Guggulsterone,1TBDMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3214.5Semi standard non polar33892256
Guggulsterone,1TBDMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3008.3Standard non polar33892256
Guggulsterone,1TBDMS,isomer #2CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3446.1Standard polar33892256
Guggulsterone,2TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3402.9Semi standard non polar33892256
Guggulsterone,2TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3216.9Standard non polar33892256
Guggulsterone,2TBDMS,isomer #1CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C3555.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guggulsterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0200-0459000000-ee86b2088f6ad3cdf31d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guggulsterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 10V, Positive-QTOFsplash10-0006-1039000000-952388fe83cbda93ea212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 20V, Positive-QTOFsplash10-00ov-1279000000-5728b5f9167d8cb788902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 40V, Positive-QTOFsplash10-0a6r-9083000000-b8990378d7107ffa738d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 10V, Negative-QTOFsplash10-0006-0029000000-5338c79160c73600c4b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 20V, Negative-QTOFsplash10-000f-0069000000-32d9482c72cfc85099ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 40V, Negative-QTOFsplash10-00kf-2090000000-69c0d68769a4ff1f7ec62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 10V, Negative-QTOFsplash10-0006-0019000000-91e1f5ec96b7e91e60842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 20V, Negative-QTOFsplash10-001l-0089000000-b763db8304fe27efa3a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 40V, Negative-QTOFsplash10-001u-0090000000-a41631240a8cd7b564092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 10V, Positive-QTOFsplash10-0006-0009000000-2538c557c24fab48c6bf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 20V, Positive-QTOFsplash10-01r7-1389000000-a0a95688ed26bb6668962021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guggulsterone 40V, Positive-QTOFsplash10-0006-9430000000-3ba9301f7512c0faae5c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023055
KNApSAcK IDC00047241
Chemspider ID558777
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuggulsterone
METLIN IDNot Available
PubChem Compound643658
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1903101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17475558 ]
  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. [PubMed:15322087 ]