{[hydroxy({[(2E,6E,10E)-3-(2H3)methyl-7,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

• ChemBase ID: 169619
• Molecular Formular: C20H36O7P2
• Molecular Mass: 450.443162
• Monoisotopic Mass: 450.19362675
• SMILES: C(=C\COP(=O)(OP(=O)(O)O)O)(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C
• Canonical SMILES: C/C(=C\CC/C(=C/COP(=O)(OP(=O)(O)O)O)/C)/CC/C=C(/CCC=C(C)C)\C
• InChI: InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+
• InChIKey: OINNEUNVOZHBOX-QIRCYJPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[hydroxy({[(2E,6E,10E)-3-(^2H₃)methyl-7,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: {hydroxy[(2E,6E,10E)-3-(^2H₃)methyl-7,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-yl]oxyphosphoryl}oxyphosphonic acid
• Synonyms: Diphosphoric Acid P-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl-d3] Ester Ammonium Salt; Diphosphoric Acid Mono[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl-d3] Ester Triammonium Salt; Geranylgeranyl Pyrophosphate-d3 Triammonium Salt

Database IDs

• PubChem SID: 162263751
• PubChem CID: 71317064

CALCULATED PROPERTIES

• Acid pKa: 1.7672187
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.86993253
• LogD (pH = 7.4): 0.24226335
• Log P: 5.2764473
• Molar Refractivity: 120.5331 cm^3
• Polarizability: 45.936985 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G367602

A labelled intermediate in terpene biosynthesis. A biosynthetic intermediate of Fusicoccins.

REFERENCES

• Casey, P., et al.: J. Biol. Chem., 271, 5289 (1996)
• Stephens, D., et al.: Science, 300, 82 (1996)
• Rose, M., et al.: J. Peptide Res., 65, 529 (1996)