(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(2H4)ethyl]-2,15-dimethyl(14-2H)tetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 176894
• Molecular Formular: C27H44O8
• Molecular Mass: 496.63346
• Monoisotopic Mass: 496.30361837
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(O)C)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13?,14-,15-,16+,17-,18+,19+,20+,21+,22-,23+,25-,26+,27-/m1/s1
• InChIKey: ZFFFJLDTCLJDHL-WPYOCMOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyl(14-^2H)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyl(14-^2H)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (3α,5β,20S)-20-Hydroxypregnan-3-yl-d5 β-D-Glucopyranosiduronic Acid; 20α-Hydroxy-5β-pregnan-3α-yl-d5 β-D-Glucopyranosiduronic Acid; 5β-Pregnane-3α,20α-diol-d5 Glucuronide; Pregnanediol-d5 3-Glucuronide; Pregnanediol-d5 3α-Monoglucuronide; Pregnanediol-d5-3α-Glucuronide; Pregnanediol-d5-3α-Glucuronoside; Pregnanediol-d5 3α-O-β-D-Glucuronide

Database IDs

• PubChem SID: 164232804
• PubChem CID: 71751755

CALCULATED PROPERTIES

• Acid pKa: 3.4672575
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.3057332
• LogD (pH = 7.4): -1.0560421
• Log P: 2.328876
• Molar Refractivity: 126.2155 cm^3
• Polarizability: 51.280586 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P705142

Labelled Pregnanediol 3α-O-β-D-Glucuronide, the glucuronide conjugate of Pregnanediol (P705130). Levels of Pregnanediol 3α-O-β-D-Glucuronide can be used to monitor the reproductive status of dairy cows. 3α-O-β-D-Glucuronide can be used (as an alternative

REFERENCES

• Yang, C.J. et al.: Asian-Austral. J. Anim. Sci., 17, 460 (2004)
• Miro, F. et al.: Clin. Chem. Lab. Med., 42, 1043 (2004)