2.0 2012-10-10 12:23:30 -0600 2015-06-03 17:26:15 -0600 ECMDB23240 M2MDB003630 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in E. coli had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of E. coli. (2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoate (2R,3S,4R,5R,6R)-3-Hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoic acid 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphate 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid 2,3-Bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphoric acid 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphate 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphate 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphate 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid 2,3-Diacylglucosamine 1-phosphate 2,3-Diacylglucosamine 1-phosphoric acid 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-a-D-glucopyranose 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-alpha-D-glucopyranose 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-α-D-glucopyranose Lipid X C34H66NO12P 711.8611 711.432263093 {[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid lipid X CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1 HEHQDWUWJVPREQ-XQJZMFRCSA-N Membrane logp 4.38 ALOGPS logs -5.05 ALOGPS solubility 6.33e-03 g/l ALOGPS logp 5.82 ChemAxon pka_strongest_acidic 1.18 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac {[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 711.8611 ChemAxon mono_mass 711.432263093 ChemAxon smiles CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC ChemAxon formula C34H66NO12P ChemAxon inchi InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1 ChemAxon inchikey HEHQDWUWJVPREQ-XQJZMFRCSA-N ChemAxon polar_surface_area 212.31 ChemAxon refractivity 180.56 ChemAxon polarizability 80.1 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1084451 Specdb::EiMs 4268 Specdb::NmrOneD 308831 Specdb::NmrOneD 308832 Specdb::NmrOneD 308833 Specdb::NmrOneD 308834 Specdb::NmrOneD 308835 Specdb::NmrOneD 308836 Specdb::NmrOneD 308837 Specdb::NmrOneD 308838 Specdb::NmrOneD 308839 Specdb::NmrOneD 308840 Specdb::NmrOneD 308841 Specdb::NmrOneD 308842 Specdb::NmrOneD 308843 Specdb::NmrOneD 308844 Specdb::NmrOneD 308845 Specdb::NmrOneD 308846 Specdb::NmrOneD 308847 Specdb::NmrOneD 308848 Specdb::NmrOneD 308849 Specdb::NmrOneD 308850 Specdb::MsMs 26228 Specdb::MsMs 26229 Specdb::MsMs 26230 Specdb::MsMs 32786 Specdb::MsMs 32787 Specdb::MsMs 32788 C04824 LP5 Lipid-A-disaccharide synthase P10441 LPXB_ECOLI lpxB http://ecmdb.ca/proteins/P10441.xml UDP-2,3-diacylglucosamine hydrolase P43341 LPXH_ECOLI lpxH http://ecmdb.ca/proteins/P43341.xml UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate > Uridine 5'-diphosphate + 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate UDP-2,3-bis((3R)-3-hydroxymyristoyl)-alpha-D-glucosamine + Water > 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate