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 methyl phosphate

• ChemBase ID: 173434
• Molecular Formular: C41H49O14P
• Molecular Mass: 796.793121
• Monoisotopic Mass: 796.28599288
• 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)OC)OC(O2)(C)C
• 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)OC
• InChI: InChI=1S/C41H49O14P/c1-9-11-20-46-24-16-18-28-30(21-24)48-31-22-25(17-19-29(31)41(28)27-15-13-12-14-26(27)38(42)53-41)54-56(43,44-8)55-37-35-33(49-39(4,5)51-35)32(47-23(3)45-10-2)34-36(37)52-40(6,7)50-34/h12-19,21-23,32-37H,9-11,20H2,1-8H3/t23?,32-,33-,34+,35-,36-,37-,41?,56?/m1/s1
• InChIKey: UALSOBIBQAPBQI-RXLBMOBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 methyl phosphate
• IUPAC Traditional name: 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 methyl phosphate
• Synonyms: 6-O-(1-Ethoxyethyl)-1,2:4,5-bis-O-(1-methylethylidene)-myo-inositol 6'-Butoxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3'-yl Methyl Phosphate; O-Methyl-O-(N-Butylfluorescein)-O-{3-[6-O-(D,L-1-ethoxyethyl)-1,2:4,5-bis-O-(1-methylethylidene)-D,L-myo-inositol]}phosphate

Database IDs

• CAS Number: 335630-21-2
• PubChem SID: 164229344
• PubChem CID: 71750247

CALCULATED PROPERTIES

• Molar Refractivity: 201.5363 cm^3
• Polarizability: 79.98919 Å^3
• Polar Surface Area: 144.9 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 6.8862014
• LogD (pH = 7.4): 6.8862014
• Log P: 6.8862014

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Foam
• Melting Point: 70-80°C

DETAILS

Toronto Research Chemicals - M294420

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)