2-oxo-2-(pyren-1-yl)ethyl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 177774
• Molecular Formular: C43H50O7
• Molecular Mass: 678.8529
• Monoisotopic Mass: 678.35565394
• SMILES: c1c2c3c4c(c1)ccc(c4ccc3ccc2)C(=O)COC(=O)C[C@@H](C[C@@H](CC[C@@H]1[C@@H]2C(=C[C@@H](C[C@@H]2OC(=O)C(C)(C)CC)C)C=C[C@@H]1C)O)O
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)OCC(=O)c1ccc3c4c1ccc1c4c(cc3)ccc1)O)O)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C43H50O7/c1-6-43(4,5)42(48)50-37-21-25(2)20-30-11-10-26(3)33(40(30)37)19-16-31(44)22-32(45)23-38(47)49-24-36(46)34-17-14-29-13-12-27-8-7-9-28-15-18-35(34)41(29)39(27)28/h7-15,17-18,20,25-26,31-33,37,40,44-45H,6,16,19,21-24H2,1-5H3/t25-,26-,31+,32+,33-,37-,40-/m0/s1
• InChIKey: WAGCOTZTJMQDOW-TXXDJFRHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2-(pyren-1-yl)ethyl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: 2-oxo-2-(pyren-1-yl)ethyl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: [1S-[1α(βS*,δS*),2α,6β,8β,8aα]]-1-pyreneacetic Acid, Anhydride with 8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid; Simvastatin, 1-Pyreneacetyl Ester

Database IDs

• CAS Number: 193682-18-7
• PubChem SID: 164233684
• PubChem CID: 46782921

CALCULATED PROPERTIES

• Acid pKa: 13.45592
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 7.482528
• LogD (pH = 7.4): 7.4825277
• Log P: 7.482528
• Molar Refractivity: 196.511 cm^3
• Polarizability: 80.076515 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S485030

Simvastatin metabolite fluorescence derivatization.

REFERENCES

• Mauro, V.F., et al.: Clin. Pharmacokin., 243, 195 (1986)
• Gamoh, K., et al.: Anal. Sci., 10, 913 (1986)
• Hoffman, W.F., et al.: J. Med. Chem., 29, 849 (1986)
• Vickers, S., et al.: Drug Metab. Dispos., 18, 138 (1986)