(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,6,6-2H4)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 139730
• Molecular Formular: C24H40O3
• Molecular Mass: 376.5726
• Monoisotopic Mass: 376.29774514
• SMILES: C1C[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC[C@@H]2C[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)C
• InChI: InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
• InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• Synonyms: (3α,5β)-3-Hydroxycholan-24-oic Acid-d4; 17β-(1-Methyl-3-carboxypropyl)etiocholan-3α-ol-d4; 3-Hydroxycholan-24-oic Acid-d4; 3α-Hydroxy-5β-cholan-24-oate-d4; 3α-Hydroxy-5β-cholan-24-oic Acid-d4; 3α-Hydroxy-5β-cholanic Acid-d4; 3α-Hydroxy-5β-cholanoic Acid-d4; 3α-Hydroxycholanic Acid-d4; NSC 683770-d4; Lithocholic Acid-d4; Lithocholic acid-2,2,4,4-d4; 石胆酸-2,2,4,4-d4

Database IDs

• CAS Number: 83701-16-0
• MDL Number: MFCD00190473
• PubChem SID: 24881239; 162233978
• PubChem CID: 16217405

CALCULATED PROPERTIES

• Acid pKa: 4.7910433
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.2362366
• LogD (pH = 7.4): 2.4612968
• Log P: 5.0220704
• Molar Refractivity: 107.6813 cm^3
• Polarizability: 43.144962 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 184-186 °C(lit.); 188-190°C
• Mass Shift: M+4

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Isotopic Purity: 98 atom % D
• Mol. Weight: mol wt 380.55 by atom % calculation
• Empirical Formula (Hill Notation): C24D4H36O3

DETAILS

Sigma Aldrich - 589349

Packaging
500 mg in glass bottle
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - L469182

A labelled cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

REFERENCES

• Brindle, J., et al.: Nat. Med., 12, 1439 (2002)
• Lindon, J., et al.: Biomarkers, 9, 1 (2002)
• Holmes, E., et al.: Cell, 134, 714 (2002)