1.0 2011-09-21 01:44:53 UTC 2015-07-21 06:59:32 UTC FDB028782 (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol (Man2GlcNAc2-Dol) is an isoprene-based lipid where an oligosaccharide moiety Man2GlcNAc2 is linked to dolichol lipid via a pyrophosphate linkage. Man2GlcNAc2-Dol is an intermediate in dolichyl-diphosphooligosaccaride biosynthesis pathway and synthesis of N-glycans. The biosynthetic pathway for this lipid-linked precursor begins with the phosphorylation of dolichol, followed by stepwise addition of sugar residues to form the product dolichyl-diphosphooligosaccharide. This pathway is of particular interest in humans, because defects in the glycosyltransferases involved lead to congenital disorders of N-glycosylation of proteins. In this pathway, (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol is formed from Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol via reaction with Dolichyl β-D-mannosyl phosphate. In the next step, one more mannose residue is added to Man2GlcNAc2-Dol via reaction with Dolichyl β-D-mannosyl phosphate. (Adapted from Human Cyc) [HMDB] C108H180N2O27P2 2000.5295 1999.224871588 {[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid [(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)OP(=O)(O)OP(=O)(O)OCCC(C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C108H180N2O27P2/c1-71(2)35-20-36-72(3)37-21-38-73(4)39-22-40-74(5)41-23-42-75(6)43-24-44-76(7)45-25-46-77(8)47-26-48-78(9)49-27-50-79(10)51-28-52-80(11)53-29-54-81(12)55-30-56-82(13)57-31-58-83(14)59-32-60-84(15)61-33-62-85(16)63-34-64-86(17)65-66-128-138(124,125)137-139(126,127)136-106-94(110-88(19)116)98(120)102(92(70-114)132-106)133-105-93(109-87(18)115)97(119)103(91(69-113)131-105)134-108-101(123)104(96(118)90(68-112)130-108)135-107-100(122)99(121)95(117)89(67-111)129-107/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,86,89-108,111-114,117-123H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-70H2,1-19H3,(H,109,115)(H,110,116)(H,124,125)(H,126,127)/b72-37+,73-39+,74-41+,75-43+,76-45+,77-47+,78-49+,79-51+,80-53+,81-55+,82-57+,83-59+,84-61+,85-63+/t86?,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99+,100+,101+,102-,103-,104+,105+,106+,107-,108+/m1/s1 ZTJFEYPCTFISRM-FSEKKYFOSA-N belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. Polyprenyl phospho carbohydrates Organic compounds Lipids and lipid-like molecules Prenol lipids Polyprenols Aliphatic heteromonocyclic compounds Acetals Acetamides Carbonyl compounds Dolichyl diphosphates Hydrocarbon derivatives Monoalkyl phosphates N-acyl-alpha-hexosamines O-glycosyl compounds Oligosaccharide phosphates Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Polyprenyl monophosphates Polyterpenoids Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Carbonyl group Carboxamide group Carboxylic acid derivative Dolichyl diphosphate Glycosyl compound Hydrocarbon derivative Monoalkyl phosphate N-acyl-alpha-hexosamine O-glycosyl compound Oligosaccharide Oligosaccharide phosphate Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Polyol Polyprenyl monophosphate Polyprenyl phosphate skeleton Polyprenyl phospho carbohydrate Polyprenyl phospho oligosaccharide Polyterpenoid Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp 7.24 ALOGPS logs -5.81 ALOGPS solubility 3.07e-03 g/l ALOGPS logp 17.52 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid ChemAxon average_mass 2000.5295 ChemAxon mono_mass 1999.224871588 ChemAxon smiles OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)OP(=O)(O)OP(=O)(O)OCCC(C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C108H180N2O27P2 ChemAxon inchi InChI=1S/C108H180N2O27P2/c1-71(2)35-20-36-72(3)37-21-38-73(4)39-22-40-74(5)41-23-42-75(6)43-24-44-76(7)45-25-46-77(8)47-26-48-78(9)49-27-50-79(10)51-28-52-80(11)53-29-54-81(12)55-30-56-82(13)57-31-58-83(14)59-32-60-84(15)61-33-62-85(16)63-34-64-86(17)65-66-128-138(124,125)137-139(126,127)136-106-94(110-88(19)116)98(120)102(92(70-114)132-106)133-105-93(109-87(18)115)97(119)103(91(69-113)131-105)134-108-101(123)104(96(118)90(68-112)130-108)135-107-100(122)99(121)95(117)89(67-111)129-107/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,86,89-108,111-114,117-123H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-70H2,1-19H3,(H,109,115)(H,110,116)(H,124,125)(H,126,127)/b72-37+,73-39+,74-41+,75-43+,76-45+,77-47+,78-49+,79-51+,80-53+,81-55+,82-57+,83-59+,84-61+,85-63+/t86?,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99+,100+,101+,102-,103-,104+,105+,106+,107-,108+/m1/s1 ChemAxon inchikey ZTJFEYPCTFISRM-FSEKKYFOSA-N ChemAxon polar_surface_area 447.63 ChemAxon refractivity 557.06 ChemAxon polarizability 233.5 ChemAxon rotatable_bond_count 65 ChemAxon acceptor_count 24 ChemAxon donor_count 15 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 287563 Specdb::MsMs 287564 Specdb::MsMs 287565 Specdb::MsMs 326437 Specdb::MsMs 326438 Specdb::MsMs 326439 Specdb::MsMs 2696058 Specdb::MsMs 2696059 Specdb::MsMs 2696060 Specdb::MsMs 2982518 Specdb::MsMs 2982519 Specdb::MsMs 2982520 HMDB12118 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