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

• ChemBase ID: 127548
• Molecular Formular: C20H36O7P2
• Molecular Mass: 450.443162
• Monoisotopic Mass: 450.19362675
• SMILES: O=P(O)(O)OP(=O)(O)OC/C=C(/CC/C=C(\C)/CC/C=C(\C)/CCC=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)
• InChIKey: OINNEUNVOZHBOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({hydroxy[(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)oxy]phosphoryl}oxy)phosphonic acid; {[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: geranylgeranyl diphosphate
• Synonyms: Diphosphoric Acid P-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl] Ester Ammonium Salt; Diphosphoric Acid Mono[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl] Ester Triammonium Salt; Geranylgeranyl Pyrophosphate Triammonium Salt; Geranylgeranyl pyrophosphate; GGPP; all trans-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl pyrophosphate ammonium salt; Geranylgeranyl pyrophosphate ammonium salt

Database IDs

• CAS Number: 313263-08-0; 6699-20-3(freeacid); 6699-20-3
• EC Number: 200-659-6
• MDL Number: MFCD00156114
• PubChem SID: 24895243; 162221867
• PubChem CID: 447277
• CHEBI ID: 48861
• Chemspider ID: 394418
• MeSH Name: geranylgeranyl+pyrophosphate
• Wikipedia Title: Geranylgeranyl_pyrophosphate

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

PROPERTIES

Physical Property

• Apperance: solution
• Flash Point: 11 °C; 51.8 °F

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301 + H311 + H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (TLC)
• Concentration: ~1 mg/mL in methanol: NH4OH (7:3)
• Packaging: vial of 200 μg

DETAILS

Sigma Aldrich - G6025

Biochem/physiol Actions
Isoprenoid from the intracellular mevalonate pathway used for prenylation of several low molecular weight G proteins, including Ras. Intermediate in terpene biosynthesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G6025.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G367600

Geranylgeranyl pyrophosphate is the metabolic precursor of all diterpenes.

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)