(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 135995
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: [C@H]1(CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H](C[C@@H]2C1)O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
• InChIKey: RUDATBOHQWOJDD-BSWAIDMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)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,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• Synonyms: (3α,5β,7α)-3,7-Dihydroxycholan-24-oic Acid-d5; (+)-Chenodeoxycholic Acid-d5; 17β-(1-Methyl-3-carboxypropyl)etiocholane-3α,7α-diol-d5; Chenodeoxycholic Acid-d5; CDC-d5; Chendol-d5; Chenodiol-d5; Chenocol-d5; Fluibil-d5; Chenodeoxycholic Acid-d5 (Major); Chenodeoxycholic-2,2,3,4,4-d5 acid; 鹅去氧胆酸-2,2,3,4,4-d5

Database IDs

• CAS Number: 52840-12-7
• MDL Number: MFCD08702893
• PubChem SID: 162230266
• PubChem CID: 71309530

CALCULATED PROPERTIES

• Acid pKa: 4.595946
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7592297
• LogD (pH = 7.4): 0.98345095
• Log P: 3.7133055
• Molar Refractivity: 109.2738 cm^3
• Polarizability: 43.768806 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 110-112°C; 165-167 °C(lit.)
• Mass Shift: M+5

Safety Information

• Storage Condition: Refrigerator

Product Information

• Isotopic Purity: 98 atom % D
• Mol. Weight: mol wt 397.50 by atom % calculation
• Empirical Formula (Hill Notation): C24D5H35O4

DETAILS

Sigma Aldrich - 617024

Packaging
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 - C291903

Labelled Chenodiol (Chenodeoxycholic acid). A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates i

REFERENCES

• Danzinger, et al.: N. Engl. J. Med., 286, 1 (1972)
• Iser, J.H., et al.: Drugs, 21, 90 (1972)
• Tint, G.S., et al.: Gastroenterology, 91, 1007 (1972)