(2E,6E)-farnesyl diphosphate
IUPAC 名称
{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
描述
Farnesyl diphosphate, also known as (2e,6e)-farnesyl pyrophosphate or trans-trans-farnesyl diphosphate, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, farnesyl diphosphate is considered to be an isoprenoid lipid molecule. Farnesyl diphosphate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Farnesyl diphosphate can be found in a number of food items such as common sage, fenugreek, oil-seed camellia, and papaya, which makes farnesyl diphosphate a potential biomarker for the consumption of these food products. Farnesyl diphosphate can be found primarily in blood, as well as in human neuron and testes tissues. Farnesyl diphosphate exists in all living species, ranging from bacteria to humans. In humans, farnesyl diphosphate is involved in several metabolic pathways, some of which include risedronate action pathway, porphyrin metabolism, cerivastatin action pathway, and fluvastatin action pathway. Farnesyl diphosphate is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, chondrodysplasia punctata II, X linked dominant (CDPX2), CHILD syndrome, and hereditary coproporphyria (HCP). Farnesyl diphosphate is used in the synthesis of CoQ (part of the electron transport chain), as well as being the immediate precursor of squalene (via the enzyme squalene synthase), dehydrodolichol diphosphate (a precursor of dolichol, which transports proteins to the ER lumen for N-glycosylation), and geranylgeranyl pyrophosphate (GGPP) .
异构
[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI标识符
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
键
VWFJDQUYCIWHTN-YFVJMOTDSA-N