(2S,3S,4S,5R,6S)-6-{[(3S,4E,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(3R,5R)-3,5-dihydroxycyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2,3-dimethylhept-4-en-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176161
• Molecular Formular: C33H52O9
• Molecular Mass: 592.76058
• Monoisotopic Mass: 592.36113324
• SMILES: C1[C@H](C[C@@H](C/C/1=C\C=C\1/CCC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(C)C)C)C)C)O)O
• Canonical SMILES: O[C@H]1C[C@H](O)C/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C33H52O9/c1-18(8-9-19(2)32(3,4)42-31-28(38)26(36)27(37)29(41-31)30(39)40)24-12-13-25-21(7-6-14-33(24,25)5)11-10-20-15-22(34)17-23(35)16-20/h8-11,18-19,22-29,31,34-38H,6-7,12-17H2,1-5H3,(H,39,40)/b9-8+,21-11+/t18-,19+,22-,23-,24-,25+,26+,27+,28-,29+,31+,33-/m1/s1
• InChIKey: AZJXNIVOZPYUJN-ILMLGNIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(3S,4E,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(3R,5R)-3,5-dihydroxycyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2,3-dimethylhept-4-en-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(3S,4E,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(3R,5R)-3,5-dihydroxycyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2,3-dimethylhept-4-en-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1R,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-Octahydro-1-[(1R,2E,4S)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol 25-β-D-Glucuronide; 1α,25-Dihydroxy-19-nor-vitamin D2 25-β-D-Glucuronide; Zemplar 25-β-D-Glucuronide; Paricalcitol 25-β-D-Glucuronide

Database IDs

• CAS Number: 1260588-15-5
• PubChem SID: 164232071
• PubChem CID: 71751431

CALCULATED PROPERTIES

• Acid pKa: 3.7092464
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 1.0180767
• LogD (pH = 7.4): -0.4937807
• Log P: 2.8079503
• Molar Refractivity: 160.2293 cm^3
• Polarizability: 62.910744 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P195310

The glucuonide metabolite of Paricalcitol (P195300) in mammalian bile.

REFERENCES

• LeVan L.W., et al.: Biochemistry, 20, 222 (1981)
• Litwiller, R.D., J. Biol. Chem., 257, 7491 (1981)