2.0 2012-05-31 14:51:28 -0600 2015-06-03 17:20:19 -0600 ECMDB20576 M2MDB001379 L-Ara4N-modified KDO2-Lipid A L-ara4n-modified kdo2-lipid a is a member of the chemical class known as Hexose Oligosaccharides. These are oligosaccharides in which the saccharide units are hexoses. α-Kdo-(2→4)-α-Kdo-(2→6)-lipid IIA α-kdo-(2→4)-α-kdo-(2→6)-lipid iia a-kdo-(2->4)-a-kdo-(2->6)-lipid a Alpha-KDO-(2->4)-alpha-KDO-(2->6)-lipid A L-Ara4n-modified (kdo)2-lipid a L-Ara4N-modified (KDO)2-Lipid A α-kdo-(2->4)-α-kdo-(2->6)-lipid a C120H220N4O45P2 2500.9781 2499.452484074 2-{[3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-6-{[6-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid 2-[(3-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-6-[(6-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl)methoxy]-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl)methoxy]-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP(O)(=O)OC2OCC(N)C(O)C2O)C(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(O)=O)C(O)C(O2)C(O)CO)C(O)=O)OC(OCC2OC(OP(O)(=O)OC3OCC(N)C(O)C3O)C(N=C(O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)C1N=C(O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC InChI=1S/C120H220N4O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(135)158-84(66-60-54-48-42-35-29-23-17-11-5)72-98(137)162-112-100(124-94(133)71-83(65-59-53-47-41-34-28-22-16-10-4)157-95(134)67-61-55-49-43-36-30-24-18-12-6)113(160-92(110(112)166-170(149,150)168-115-106(143)101(138)85(121)77-153-115)80-156-119(117(145)146)74-90(104(141)109(164-119)89(131)76-126)163-120(118(147)148)73-87(129)103(140)108(165-120)88(130)75-125)155-79-91-105(142)111(161-97(136)70-82(128)64-58-52-46-40-33-27-21-15-9-3)99(123-93(132)69-81(127)63-57-51-45-39-32-26-20-14-8-2)114(159-91)167-171(151,152)169-116-107(144)102(139)86(122)78-154-116/h81-92,99-116,125-131,138-144H,7-80,121-122H2,1-6H3,(H,123,132)(H,124,133)(H,145,146)(H,147,148)(H,149,150)(H,151,152) RYVJLJVPSMBXLB-UHFFFAOYSA-N Inner membrane Membrane Outer membrane logp 0.62 ALOGPS logs -4.52 ALOGPS solubility 7.61e-02 g/l ALOGPS logp 17.07 ChemAxon pka_strongest_acidic 1.05 ChemAxon pka_strongest_basic 9.09 ChemAxon iupac 2-{[3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-6-{[6-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid ChemAxon average_mass 2500.9781 ChemAxon mono_mass 2499.452484074 ChemAxon smiles CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP(O)(=O)OC2OCC(N)C(O)C2O)C(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(O)=O)C(O)C(O2)C(O)CO)C(O)=O)OC(OCC2OC(OP(O)(=O)OC3OCC(N)C(O)C3O)C(N=C(O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)C1N=C(O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC ChemAxon formula C120H220N4O45P2 ChemAxon inchi InChI=1S/C120H220N4O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(135)158-84(66-60-54-48-42-35-29-23-17-11-5)72-98(137)162-112-100(124-94(133)71-83(65-59-53-47-41-34-28-22-16-10-4)157-95(134)67-61-55-49-43-36-30-24-18-12-6)113(160-92(110(112)166-170(149,150)168-115-106(143)101(138)85(121)77-153-115)80-156-119(117(145)146)74-90(104(141)109(164-119)89(131)76-126)163-120(118(147)148)73-87(129)103(140)108(165-120)88(130)75-125)155-79-91-105(142)111(161-97(136)70-82(128)64-58-52-46-40-33-27-21-15-9-3)99(123-93(132)69-81(127)63-57-51-45-39-32-26-20-14-8-2)114(159-91)167-171(151,152)169-116-107(144)102(139)86(122)78-154-116/h81-92,99-116,125-131,138-144H,7-80,121-122H2,1-6H3,(H,123,132)(H,124,133)(H,145,146)(H,147,148)(H,149,150)(H,151,152) ChemAxon inchikey RYVJLJVPSMBXLB-UHFFFAOYSA-N ChemAxon polar_surface_area 774.83 ChemAxon refractivity 620.32 ChemAxon polarizability 279.18 ChemAxon rotatable_bond_count 102 ChemAxon acceptor_count 41 ChemAxon donor_count 22 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon polymyxin resistance UDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid A PW002052 Metabolic polymyxin resistance PWY0-1338 Specdb::MsMs 3642258 Specdb::MsMs 3642259 Specdb::MsMs 3642260 Specdb::MsMs 3642261 Specdb::MsMs 3642262 Specdb::MsMs 3642263 656478 570865 L-ARA4N-MODIFIED-KDO2-LIPID-A Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase P76473 ARNT_ECOLI arnT http://ecmdb.ca/proteins/P76473.xml KDO2-Lipid A + 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate > L-Ara4N-modified KDO2-Lipid A + Di-trans,poly-cis-undecaprenyl phosphate RXN0-2001 2 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + (KDO)2-lipid A >2 di-trans,octa-cis-undecaprenyl diphosphate + L-Ara4N-modified KDO2-Lipid A PW_R005995