sodium (3R,5S,6E)-7-[3-(4-fluorophenyl)-5-hydroxy-1-[(2H7)propan-2-yl]-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 170229
• Molecular Formular: C24H25FNNaO5
• Molecular Mass: 449.4471732
• Monoisotopic Mass: 449.16144541
• SMILES: c1c(ccc2c1c(c(n2C(C)C)/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F)O.[Na+]
• Canonical SMILES: O[C@H](C[C@@H](/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)ccc(c2)O)O)CC(=O)[O-].[Na+]
• InChI: InChI=1S/C24H26FNO5.Na/c1-14(2)26-21-9-7-18(28)12-20(21)24(15-3-5-16(25)6-4-15)22(26)10-8-17(27)11-19(29)13-23(30)31;/h3-10,12,14,17,19,27-29H,11,13H2,1-2H3,(H,30,31);/q;+1/p-1/b10-8+;/t17-,19-;/m1./s1
• InChIKey: MHHBOCPYDHYTEO-XVCCDYDGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[3-(4-fluorophenyl)-5-hydroxy-1-[(^2H₇)propan-2-yl]-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[3-(4-fluorophenyl)-5-hydroxy-1-[(^2H₇)propan-2-yl]indol-2-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: (3R,5S,6E)-rel-7-[3-(4-Fluorophenyl)-5-hydroxy-1-(1-methylethyl-d7)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; [R*,S*-(E)]-(±)-7-[3-(4-Fluorophenyl)-5-hydroxy-1-(1-methylethyl-d7)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic Acid Monosodium Salt; 5-Hydroxy Fluvastatin-d7 Sodium Salt

Database IDs

• PubChem SID: 164226139
• PubChem CID: 71748880

CALCULATED PROPERTIES

• Acid pKa: 4.5585394
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.5349536
• LogD (pH = 7.4): 0.7581066
• Log P: 3.5223837
• Molar Refractivity: 127.6733 cm^3
• Polarizability: 46.609222 Å^3
• Polar Surface Area: 105.75 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825522

Labelled 5-Hydroxy Fluvastatin. 5-Hydroxy Fluvastatin is a metabolite of Fluvastatin (F601250) with inhibitory effects on the formation of several reactive oxygen species (ROS).

REFERENCES

• Nakashima, A. et al.: Life Sci., 69, 1381 (2001)
• Nakashima, A. et al.: Yakug. Zas., 121, 113 (2001)