1.02011-09-21 00:36:36 UTC2015-07-21 06:57:55 UTCFDB023901Dolichol phosphateDolichol phosphate is the most prevalent polyisoprenyl-glycosyl carrier found in mammals. It is involved in reactions such as the C-4 and O-mannosylation of proteins, the formation of glycosylphosphatidylinositol (GPI) anchors and the N-glycosylation of proteins. The chain length of eukaryotic dolichol molecules differs from 14 to 17 isoprene units in unicellular organisms like yeast whereas mammalian cells produce dolichol with 18-21 isoprene units. During the de novo synthesis of dolichol in eukaryotes, farnesyl pyrophosphate, a metabolite of cholesterol biosynthesis, is elongated by successive condensations to isopentenyl pyrophosphate molecules. These reactions are catalyzed by cis-isopentenyltransferases. After the polyisoprene pyrophosphate chain has reached its final length, both phosphate residues are released by mono- or pyrophosphatases. The isoprene unit of the polyprenol is then reduced by a nicotinamide adenine dinucleotide phosphate (NADPH)-dependent microsomal reductase. The final step in dolichol phosphate synthesis is catalyzed by dolichol kinase (DK1), an enzyme that transfers a phosphate from choline-phosphate cytidine triphosphate (CTP) to dolichol. Once synthesized, dolichol phosphate can react with cytosolic GDP-mannose in the endoplasmic reticulum membrane to form dolichyl phosphate D-mannose. A new inherited metabolic disorder, Dolichol kinase (DK1) deficiency has recently been discovered. Affected patients present with a very severe clinical phenotype, with death in early infancy. Symptoms include secondary microencephaly, dry, thin, parchmentlike skin, hyperkeratosis, minimal hair growth and muscular hypotonia. (PMID: 17273964) [HMDB]Dolichol monoatedolichol monophosphateDolichol-ateDolichol-Pdolichol-phosphateDolichol-PO4Dolichyl-atedolichyl-phosphateDolychol ateDolychol phosphate(C5H8)nC10H21O4P34457-14-2CC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)CInChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)/b14-9+DZHSRPJGCZHWOM-NTEUORMPSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.SesquiterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsSesquiterpenoidsAliphatic acyclic compoundsHydrocarbon derivativesMonoalkyl phosphatesOrganic oxidesOrganooxygen compoundsAliphatic acyclic compoundAlkyl phosphateFarsesane sesquiterpenoidHydrocarbon derivativeMonoalkyl phosphateOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganooxygen compoundPhosphoric acid esterSesquiterpenoidSolidlogp3.40logs-3.80solubility4.85e-02 g/lsmilesCC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)Cformula(C5H8)nC10H21O4PinchiInChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)/b14-9+inchikeyDZHSRPJGCZHWOM-NTEUORMPSA-Nformal_charge0Specdb::CMs3455Specdb::MsMs182532Specdb::MsMs182533Specdb::MsMs182534Specdb::MsMs2286316Specdb::MsMs2286317Specdb::MsMs2286318Specdb::MsMs180198Specdb::MsMs180199Specdb::MsMs180200Specdb::MsMs3082089Specdb::MsMs3082090Specdb::MsMs3082091HMDB06353#<Reference:0x000055567641fdd0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Dolichol-phosphate mannosyltransferaseO60762DPM1Dolichyl-phosphate beta-glucosyltransferaseQ9Y673ALG5Dolichyldiphosphatase 1Q86YN1DOLPP1UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferaseQ9H3H5DPAGT1