(1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,13-dione

• ChemBase ID: 153785
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C/C=C\1/C(=O)C[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C
• Canonical SMILES: C/C=C\1/C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/t15-,17+,18+,20+,21-/m1/s1
• InChIKey: WDXRGPWQVHZTQJ-NRJJLHBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,13-dione
• IUPAC Traditional name: (1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,13-dione
• Synonyms: (17Z)-Pregna-4,17(20)-diene-3,16-dione; 4,17(20)-trans-Pregnadiene-3,16-dione; (Z)-Guggulsterone; (17E)-Pregna-4,17(20)-diene-3,16-dione; (E)-Guggulsterone

Database IDs

• CAS Number: 39025-24-6; 39025-23-5
• MDL Number: MFCD01310757; MFCD01310758
• PubChem SID: 24278392; 162247924
• PubChem CID: 6439929

CALCULATED PROPERTIES

• Acid pKa: 19.042126
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.254959
• LogD (pH = 7.4): 4.254959
• Log P: 4.254959
• Molar Refractivity: 93.6071 cm^3
• Polarizability: 36.159924 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble5 mg/mL
• Apperance: light yellow powder; white to off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37
• Safety Statements: 36
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥89% (HPLC); ≥95% (HPLC)
• Impurities: ≤5.4% E-form
• Empirical Formula (Hill Notation): C21H28O2

DETAILS

Sigma Aldrich - G4923

Biochem/physiol Actions
Naturally occuring bioactive plant sterol isolated from the gum resin of guggul (Commiphora wightii). Antihyperlipidemic. Induces the expression of human CYP3A.1. Guggulsterone potently reverses multi-drug resistance in a number of human cancer cell lines, extending the efficacy of chemotherapy.2

Sigma Aldrich - G5168

Biochem/physiol Actions
(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator.