2.0 2012-10-10 12:18:13 -0600 2015-06-03 17:26:00 -0600 ECMDB23134 M2MDB003524 UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine is an intermediate in Lipid IVA synthesis. It is a substrate for the enzyme UDP-2,3-diacylglucosamine diphosphatase which catalyzes the reaction UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + H2O = 2,3-bis[(3R)-3-hydroxymyristoyl]-beta-D-glucosaminyl 1-phosphate + UMP. OH-MYRISTOYL UDP-2,3-bis(3-hydroxymyristoyl)glucosamine UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine UDP-2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosamine UDP-2,3-bis(3R)-3-hydroxymyristoyl-alpha-D-glucosamine UDP-2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosamine UDP-2,3-Bis(O-(3R)-3-hydroxymyristoyl)-a-D-glucosamine UDP-2,3-Bis(O-(3R)-3-hydroxymyristoyl)-α-D-glucosamine UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-a-D-glucosamine UDP-2,3-bisO-(3R)-3-hydroxymyristoyl-alpha-D-glucosamine UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-α-D-glucosamine UDP-2,3-diacyl-glucosamine C43H75N3O20P2 1016.0112 1015.441914879 (3R)-N-[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanecarboximidate (3R)-N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanecarboximidate [H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/p-2/t29-,30-,31-,32-,36-,37-,38-,39-,40-,41-,42-/m1/s1 KOJCFMYSTWNMQW-RUAJDYCTSA-L Membrane logp 3.32 ALOGPS logs -3.21 ALOGPS solubility 6.46e-01 g/l ALOGPS logp 5.06 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (3R)-N-[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanecarboximidate ChemAxon average_mass 1016.0112 ChemAxon mono_mass 1015.441914879 ChemAxon smiles [H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC ChemAxon formula C43H75N3O20P2 ChemAxon inchi InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/p-2/t29-,30-,31-,32-,36-,37-,38-,39-,40-,41-,42-/m1/s1 ChemAxon inchikey KOJCFMYSTWNMQW-RUAJDYCTSA-L ChemAxon polar_surface_area 359.58 ChemAxon refractivity 262.16 ChemAxon polarizability 105.07 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 18 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 297355 Specdb::NmrOneD 297356 Specdb::NmrOneD 297357 Specdb::NmrOneD 297358 Specdb::NmrOneD 297359 Specdb::NmrOneD 297360 Specdb::NmrOneD 297361 Specdb::NmrOneD 297362 Specdb::NmrOneD 297363 Specdb::NmrOneD 297364 Specdb::NmrOneD 297365 Specdb::NmrOneD 297366 Specdb::NmrOneD 297367 Specdb::NmrOneD 297368 Specdb::NmrOneD 297369 Specdb::NmrOneD 297370 Specdb::NmrOneD 297371 Specdb::NmrOneD 297372 Specdb::NmrOneD 297373 Specdb::NmrOneD 297374 Specdb::MsMs 36929 Specdb::MsMs 36930 Specdb::MsMs 36931 Specdb::MsMs 39377 Specdb::MsMs 39378 Specdb::MsMs 39379 UDP-3-O-[3-hydroxymyristoyl] glucosamine N-acyltransferase P21645 LPXD_ECOLI lpxD http://ecmdb.ca/proteins/P21645.xml (3R)-3-hydroxymyristoyl-[acyl-carrier-protein] + UDP-3-O-((3R)-hydroxymyristoyl)-alpha-D-glucosamine > UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine + a holo-[acyl-carrier-protein]