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

• ChemBase编号: 127548
• 分子式: C20H36O7P2
• 平均质量: 450.443162
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: ({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传统名: geranylgeranyl diphosphate
• 别名: 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

登记号

• CAS号: 6699-20-3; 313263-08-0; 6699-20-3(freeacid)
• EC号: 200-659-6
• MDL号: MFCD00156114
• PubChem SID: 24895243; 162221867
• PubChem CID: 447277
• CHEBI ID: 48861
• Chemspider ID: 394418
• 医学主题词(MeSH): geranylgeranyl+pyrophosphate
• 维基百科标题: Geranylgeranyl_pyrophosphate

理论计算性质

• Acid pKa: 1.7672187
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.86993253
• LogD (pH = 7.4): 0.24226335
• Log P: 5.2764473
• 摩尔折射率: 120.5331 cm^3
• 极化性: 45.936985 Å^3
• 极化表面积: 113.29 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: solution
• 闪点: 11 °C; 51.8 °F

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 1230
• 德国WGK号: 2
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25
• 安全公开号: 7-16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301 + H311 + H331-H370
• GHS警示性声明: P210-P260-P280-P301 + P310-P311
• 个人保护装置: 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
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95% (TLC)
• 浓度: ~1 mg/mL in methanol: NH4OH (7:3)
• 包装: vial of 200 μg

详细说明

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.

参考文献

• 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)