lithium(1+) ion 6'-butoxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3'-yl (1R,2S,3R,7R,8S,9S)-8-(1-ethoxyethoxy)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-yl phosphate

• ChemBase ID: 163425
• Molecular Formular: C40H46LiO14P
• Molecular Mass: 788.699601
• Monoisotopic Mass: 788.27852233
• SMILES: [C@@H]12[C@@H](OC(O2)(C)C)[C@@H](OC(C)OCC)[C@@H]2[C@H]([C@@H]1OP(=O)(Oc1ccc3c(c1)Oc1c(C43c3c(C(=O)O4)cccc3)ccc(c1)OCCCC)[O-])OC(O2)(C)C.[Li+]
• Canonical SMILES: CCCCOc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)OP(=O)(O[C@@H]1[C@@H]2OC(O[C@H]2[C@H]([C@@H]2[C@H]1OC(O2)(C)C)OC(OCC)C)(C)C)[O-].[Li+]
• InChI: InChI=1S/C40H47O14P.Li/c1-8-10-19-45-23-15-17-27-29(20-23)47-30-21-24(16-18-28(30)40(27)26-14-12-11-13-25(26)37(41)52-40)53-55(42,43)54-36-34-32(48-38(4,5)50-34)31(46-22(3)44-9-2)33-35(36)51-39(6,7)49-33;/h11-18,20-22,31-36H,8-10,19H2,1-7H3,(H,42,43);/q;+1/p-1/t22?,31-,32-,33+,34-,35-,36-,40?;/m1./s1
• InChIKey: CQZZBJUCSZDUGO-UDMMYTCWSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion 6'-butoxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3'-yl (1R,2S,3R,7R,8S,9S)-8-(1-ethoxyethoxy)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.0^3,^7]dodecan-2-yl phosphate
• IUPAC Traditional name: lithium(1+) ion 6'-butoxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl (1R,2S,3R,7R,8S,9S)-8-(1-ethoxyethoxy)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.0^3,^7]dodecan-2-yl phosphate
• Synonyms: O-(N-Butylfluorescein)-O-{3-[6-O-(D,L-1-ethoxyethyl)-1,2:4,5-bis-O-(1-methylethylidene)-D,L-myo-inositol]}phosphate, Lithium Salt

Database IDs

• PubChem SID: 162257560
• PubChem CID: 71314429

CALCULATED PROPERTIES

• Acid pKa: 1.3138417
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 4.138492
• LogD (pH = 7.4): 4.1319265
• Log P: 6.5082407
• Molar Refractivity: 195.9323 cm^3
• Polarizability: 77.80744 Å^3
• Polar Surface Area: 158.73 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Powder
• Melting Point: 200°C dec.

DETAILS

Toronto Research Chemicals - B691770

An intermediatel in the synthesis of Butyl-FLIP, a fluorogenic substrate for continuous assay of phosphatidylinositol-specific Phospholipase C.

REFERENCES

• Zalkova, T.O., et al.: Bioconjugate Chem., 12, 307 (2001)