1.0 2011-09-21 00:12:41 UTC 2015-07-21 06:57:10 UTC FDB022356 Dolichyl phosphate D-mannose Dolichyl 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 mannose dolichol phosphate mannose Dolichyl ate D-mannose Dolichyl D-mannosyl ate DPM C6H13O9P 260.1358 260.029718526 {[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid dolichyl phosphate D-mannose 908211-94-9 OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=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/s1 HXXFSFRBOHSIMQ-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 phosphates Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hexoses Hydrocarbon derivatives Monoalkyl phosphates Organic oxides Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Hexose monosaccharide Hydrocarbon derivative Monoalkyl phosphate Monosaccharide phosphate Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Oxacycle Oxane Phosphoric acid ester Polyol Primary alcohol Secondary alcohol Solid logp -2.00 ALOGPS logs -0.91 ALOGPS solubility 3.23e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.16 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H13O9P ChemAxon inchi InChI=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/s1 ChemAxon inchikey HXXFSFRBOHSIMQ-PQMKYFCFSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 46.8 ChemAxon polarizability 20.33 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20807 Specdb::CMs 37881 Specdb::CMs 159012 Specdb::CMs 1083126 Specdb::CMs 1083127 Specdb::CMs 1083128 Specdb::CMs 1083129 Specdb::CMs 1083130 Specdb::CMs 1083131 Specdb::CMs 1083132 Specdb::CMs 1083133 Specdb::CMs 1083134 Specdb::CMs 1083135 Specdb::CMs 1083136 Specdb::CMs 1083137 Specdb::CMs 1083138 Specdb::CMs 1083139 Specdb::CMs 1083140 Specdb::CMs 1083141 Specdb::CMs 1083142 Specdb::CMs 1083143 Specdb::CMs 1083144 Specdb::CMs 1083145 Specdb::CMs 1083146 Specdb::CMs 1083147 Specdb::NmrOneD 145990 Specdb::NmrOneD 145991 Specdb::NmrOneD 145992 Specdb::NmrOneD 145993 Specdb::NmrOneD 145994 Specdb::NmrOneD 145995 Specdb::NmrOneD 145996 Specdb::NmrOneD 145997 Specdb::NmrOneD 145998 Specdb::NmrOneD 145999 Specdb::NmrOneD 146000 Specdb::NmrOneD 146001 Specdb::NmrOneD 146002 Specdb::NmrOneD 146003 Specdb::NmrOneD 146004 Specdb::NmrOneD 146005 Specdb::NmrOneD 146006 Specdb::NmrOneD 146007 Specdb::NmrOneD 146008 Specdb::NmrOneD 146009 Specdb::MsMs 312352 Specdb::MsMs 312353 Specdb::MsMs 312354 Specdb::MsMs 357586 Specdb::MsMs 357587 Specdb::MsMs 357588 Specdb::MsMs 2659906 Specdb::MsMs 2659907 Specdb::MsMs 2659908 Specdb::MsMs 3018255 Specdb::MsMs 3018256 Specdb::MsMs 3018257 HMDB00994 #<Reference:0x000055ce318fb060> #<Reference:0x000055ce318faea8> 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 Dol-P-Man:Man(5)GlcNAc(2)-PP-Dol alpha-1,3-mannosyltransferase Q92685 ALG3 Dolichol-phosphate mannosyltransferase O60762 DPM1