1.02011-09-21 00:12:41 UTC2015-07-21 06:57:10 UTCFDB022356Dolichyl phosphate D-mannoseDolichyl phosphate D-mannose (DPM) is an intermediate in the biosynthesis of N-glycans. It is a substrate for dolichol-phosphate mannosyltransferase (PMID: 10835346). Dolichol-phosphate mannosyltransferase is a heterotrimeric protein embedded in the endoplasmic reticulum membrane. The first subunit of the heterotrimer appears to be the actual catalyst, and the other two subunits appear to stabilize it. More specifically, dolichol-phosphate-mannose is the donor of mannose groups in the synthesis of the dolichol pyrophosphate-linked precursor oligosaccharide in asparagine-linked glycosylation, in the synthesis of glycosyl phosphatidylinositol (GPI) anchor precursors, in protein O-mannosylation and in protein C-mannosylation. Its synthesis proceeds in two steps. First, cytosolic GDP-mannose reacts with dolichol phosphate exposed on the cytosolic face of the endoplasmic reticulum membrane to form DPM with its mannose moiety oriented toward the cytosol. The DPM molecule then flips in the endoplasmic reticulum membrane, so that its mannose moiety is in the endoplasmic reticulum lumen, accessible to the enzymes that catalyze its transfer to growing glycolipids and glycoproteins. (PMID: 11102867). Dolichyl phosphate D-mannose is also a substrate for protein O-mannosyl-transferase 2 and protein O-mannosyl-transferase 1. [HMDB]Dolichol ate mannosedolichol phosphate mannoseDolichyl ate D-mannoseDolichyl D-mannosyl ateDPMC6H13O9P260.1358260.029718526{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic aciddolichyl phosphate D-mannose908211-94-9OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1OInChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1HXXFSFRBOHSIMQ-PQMKYFCFSA-N belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.Monosaccharide phosphatesOrganic compoundsOrganic oxygen compoundsOrganooxygen compoundsCarbohydrates and carbohydrate conjugatesAliphatic heteromonocyclic compoundsHexosesHydrocarbon derivativesMonoalkyl phosphatesOrganic oxidesOxacyclic compoundsOxanesPolyolsPrimary alcoholsSecondary alcoholsAlcoholAliphatic heteromonocyclic compoundAlkyl phosphateHexose monosaccharideHydrocarbon derivativeMonoalkyl phosphateMonosaccharide phosphateOrganic oxideOrganic phosphoric acid derivativeOrganoheterocyclic compoundOxacycleOxanePhosphoric acid esterPolyolPrimary alcoholSecondary alcoholSolidlogp-2.00logs-0.91solubility3.23e+01 g/llogp-3.1pka_strongest_acidic1.16pka_strongest_basic-3iupac{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acidaverage_mass260.1358mono_mass260.029718526smilesOC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1OformulaC6H13O9PinchiInChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1inchikeyHXXFSFRBOHSIMQ-PQMKYFCFSA-Npolar_surface_area156.91refractivity46.8polarizability20.33rotatable_bond_count3acceptor_count8donor_count6physiological_charge-2formal_charge0Specdb::CMs20807Specdb::CMs37881Specdb::CMs159012Specdb::CMs1083126Specdb::CMs1083127Specdb::CMs1083128Specdb::CMs1083129Specdb::CMs1083130Specdb::CMs1083131Specdb::CMs1083132Specdb::CMs1083133Specdb::CMs1083134Specdb::CMs1083135Specdb::CMs1083136Specdb::CMs1083137Specdb::CMs1083138Specdb::CMs1083139Specdb::CMs1083140Specdb::CMs1083141Specdb::CMs1083142Specdb::CMs1083143Specdb::CMs1083144Specdb::CMs1083145Specdb::CMs1083146Specdb::CMs1083147Specdb::MsMs312352Specdb::MsMs312353Specdb::MsMs312354Specdb::MsMs357586Specdb::MsMs357587Specdb::MsMs357588Specdb::MsMs2659906Specdb::MsMs2659907Specdb::MsMs2659908Specdb::MsMs3018255Specdb::MsMs3018256Specdb::MsMs3018257Specdb::NmrOneD145990Specdb::NmrOneD145991Specdb::NmrOneD145992Specdb::NmrOneD145993Specdb::NmrOneD145994Specdb::NmrOneD145995Specdb::NmrOneD145996Specdb::NmrOneD145997Specdb::NmrOneD145998Specdb::NmrOneD145999Specdb::NmrOneD146000Specdb::NmrOneD146001Specdb::NmrOneD146002Specdb::NmrOneD146003Specdb::NmrOneD146004Specdb::NmrOneD146005Specdb::NmrOneD146006Specdb::NmrOneD146007Specdb::NmrOneD146008Specdb::NmrOneD146009HMDB00994#<Reference:0x0000555674df5050>#<Reference:0x0000555674df4c68>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 scrofa9823Dol-P-Man:Man(5)GlcNAc(2)-PP-Dol alpha-1,3-mannosyltransferaseQ92685ALG3Dolichol-phosphate mannosyltransferaseO60762DPM1