sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-6-[(2S)-1-hydroxypropan-2-yl]-5-[(2H3)methoxymethyl]-2-(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 170329
• Molecular Formular: C26H33FNNaO6
• Molecular Mass: 497.5314932
• Monoisotopic Mass: 497.21896028
• SMILES: c1(c(c(nc(c1/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)[C@H](C)CO)COC)c1ccc(cc1)F.[Na+]
• Canonical SMILES: COCc1c(c2ccc(cc2)F)c(/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)c(nc1[C@@H](CO)C)C(C)C.[Na+]
• InChI: InChI=1S/C26H34FNO6.Na/c1-15(2)25-21(10-9-19(30)11-20(31)12-23(32)33)24(17-5-7-18(27)8-6-17)22(14-34-4)26(28-25)16(3)13-29;/h5-10,15-16,19-20,29-31H,11-14H2,1-4H3,(H,32,33);/q;+1/p-1/b10-9+;/t16-,19-,20-;/m1./s1
• InChIKey: KXWIMFNOEPAPDJ-ZZDRRHRHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-6-[(2S)-1-hydroxypropan-2-yl]-5-[(^2H₃)methoxymethyl]-2-(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-6-[(2S)-1-hydroxypropan-2-yl]-2-isopropyl-5-[(^2H₃)methoxymethyl]pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-[(1S)-2-hydroxy-1-methylethyl]-5-[(methoxy-d3)-methyl]-2-(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; M-23 Metabolite-d3; Hydroxy Cerivastatin-d3 Sodium Salt

Database IDs

• PubChem SID: 164226239
• PubChem CID: 46781738

CALCULATED PROPERTIES

• Acid pKa: 4.024328
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.3443724
• LogD (pH = 7.4): -0.1670353
• Log P: 1.577836
• Molar Refractivity: 139.435 cm^3
• Polarizability: 50.28542 Å^3
• Polar Surface Area: 122.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Pale Yellow Solid
• Melting Point: 99-104°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H900252

A labelled metabolite of Cerivastatin, a competitive inhibitor of HMG-CoA reductase.

REFERENCES

• Boberg, M., et al.: Drug Metab. Dispos., 25, 321 (1997)