1.0 2011-09-21 00:36:36 UTC 2015-07-21 06:57:55 UTC FDB023901 Dolichol phosphate Dolichol 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 monoate dolichol monophosphate Dolichol-ate Dolichol-P dolichol-phosphate Dolichol-PO4 Dolichyl-ate dolichyl-phosphate Dolychol ate Dolychol phosphate (C5H8)nC10H21O4P 34457-14-2 CC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)C InChI=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. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Monoalkyl phosphates Organic oxides Organooxygen compounds Aliphatic acyclic compound Alkyl phosphate Farsesane sesquiterpenoid Hydrocarbon derivative Monoalkyl phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Sesquiterpenoid Solid logp 3.40 ALOGPS logs -3.80 ALOGPS solubility 4.85e-02 g/l ALOGPS smiles CC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)C ChemAxon formula (C5H8)nC10H21O4P ChemAxon inchi InChI=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+ ChemAxon inchikey DZHSRPJGCZHWOM-NTEUORMPSA-N ChemAxon formal_charge 0 ChemAxon Specdb::CMs 3455 Specdb::MsMs 180198 Specdb::MsMs 180199 Specdb::MsMs 180200 Specdb::MsMs 182532 Specdb::MsMs 182533 Specdb::MsMs 182534 Specdb::MsMs 2286316 Specdb::MsMs 2286317 Specdb::MsMs 2286318 Specdb::MsMs 3082089 Specdb::MsMs 3082090 Specdb::MsMs 3082091 HMDB06353 #<Reference:0x000055ce31d41fe8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Dolichol-phosphate mannosyltransferase O60762 DPM1 Dolichyl-phosphate beta-glucosyltransferase Q9Y673 ALG5 Dolichyldiphosphatase 1 Q86YN1 DOLPP1 UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase Q9H3H5 DPAGT1