(1R,2R,5S,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)-17-(prop-2-en-1-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicosane-5-carboxylic acid hydrate

• ChemBase ID: 154768
• Molecular Formular: C33H54O4
• Molecular Mass: 514.77946
• Monoisotopic Mass: 514.40221021
• SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@@H]3[C@]4(CC[C@](C([C@@H]4CC[C@]3([C@@]1(CC2)C)C)(C)C)(CC=C)O)C)C(=O)O.O
• Canonical SMILES: C=CC[C@]1(O)CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C.O
• InChI: InChI=1S/C33H52O3.H2O/c1-9-14-33(36)20-17-29(6)24(28(33,4)5)13-15-31(8)25(29)11-10-23-26-22(21(2)3)12-16-32(26,27(34)35)19-18-30(23,31)7;/h9,22-26,36H,1-2,10-20H2,3-8H3,(H,34,35);1H2/t22-,23+,24-,25+,26+,29-,30+,31+,32-,33-;/m0./s1
• InChIKey: JMELBGCTIDKOPM-RQBNYOBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)-17-(prop-2-en-1-yl)pentacyclo[11.8.0.0^2,^1^0.0^5,^9.0^1^4,^1^9]henicosane-5-carboxylic acid hydrate
• IUPAC Traditional name: (1R,2R,5S,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)-17-(prop-2-en-1-yl)pentacyclo[11.8.0.0^2,^1^0.0^5,^9.0^1^4,^1^9]henicosane-5-carboxylic acid hydrate
• Synonyms: (3?)-3-Hydroxy-3-(2-propen-1-yl)-lup-20(29)-en-28-oic acid hydrate; (3R)-3-Allyl-3-hydroxylup-20(29)-en-28-oic acid hydrate; 18 dia 2; RG-239 hydrate

Database IDs

• MDL Number: MFCD17215967
• PubChem SID: 162248906
• PubChem CID: 67993065

CALCULATED PROPERTIES

• Acid pKa: 4.748318
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.761627
• LogD (pH = 7.4): 4.9848027
• Log P: 7.583419
• Molar Refractivity: 146.4328 cm^3
• Polarizability: 58.52432 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C33H52O3 · xH2O

DETAILS

Sigma Aldrich - R0783

Biochem/physiol Actions
RG-239 is a TGR5 agonist
Semisynthetic derivative of betulinic acid (3β-allylbetulinic acid), RG-239 is an agonist at the G-protein coupled receptor TGR5. TGR5 signalling induces glucagon-like peptide-1 (GLP-1) release in brown adipose tissue, enhancing glucose tolerance and attenuating diet-induced obesity.