(2S,3S,4S,5R,6S)-6-{[(3S,5R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177614
• Molecular Formular: C28H36FN3O12S
• Molecular Mass: 657.6617432
• Monoisotopic Mass: 657.20037283
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)OC(=O)C[C@H](C[C@@H](O)/C=C/c1c(nc(nc1c1ccc(cc1)F)N(S(=O)(=O)C)C)C(C)C)O)O)O)O
• Canonical SMILES: O[C@H](C[C@@H](CC(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O)/C=C/c1c(nc(nc1c1ccc(cc1)F)N(S(=O)(=O)C)C)C(C)C
• InChI: InChI=1S/C28H36FN3O12S/c1-13(2)20-18(21(14-5-7-15(29)8-6-14)31-28(30-20)32(3)45(4,41)42)10-9-16(33)11-17(34)12-19(35)43-27-24(38)22(36)23(37)25(44-27)26(39)40/h5-10,13,16-17,22-25,27,33-34,36-38H,11-12H2,1-4H3,(H,39,40)/b10-9+/t16-,17-,22-,23-,24+,25-,27+/m0/s1
• InChIKey: AWGDNYJLUILGBY-HQVXKHOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(3S,5R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(3S,5R,6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethanesulfonamido)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(3S,5R,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoate] β-D-Glucopyranuronic Acid; ent-Rosuvastatin Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164233524
• PubChem CID: 71752116

CALCULATED PROPERTIES

• Acid pKa: 3.2476811
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -2.257218
• LogD (pH = 7.4): -3.4615073
• Log P: -0.024833092
• Molar Refractivity: 153.7369 cm^3
• Polarizability: 62.01911 Å^3
• Polar Surface Area: 237.14 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R700530

The enantiomer metabolite of Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor.