2.0 2012-07-30 14:55:24 -0600 2015-06-03 17:21:12 -0600 ECMDB21350 M2MDB001748 Phospho-heptosyl-heptosyl-kdo2-lipidA Phospho-heptosyl-heptosyl-kdo2-lipida belongs to the class of Hexose Oligosaccharides. These are oligosaccharides in which the saccharide units are hexoses. (inferred from compound structure) Phospho-heptosyl-heptosyl-kdo2-lipidA C124H219N2O54P3 2694.9679 2693.366504142 (2R,4R,5R,6R)-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-{[(3S,4S,5R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4R,5S)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylate (2R,4R,5R,6R)-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-{[(3S,4S,5R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4R,5S)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylate [H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO[C@@]3(C[C@@]([H])(OC4(CC([H])(O)C([H])(O)C([H])(O4)C([H])(O)CO)C([O-])=O)[C@@]([H])(OC4([H])OC([H])([C@@]([H])(O)CO)[C@@]([H])(O)[C@]([H])(OC5([H])OC([H])([C@@]([H])(O)CO)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(O)[C@]5([H])O)[C@]4([H])O)[C@]([H])(O3)[C@]([H])(O)CO)C([O-])=O)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC InChI=1S/C124H227N2O54P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(141)166-84(66-60-54-48-42-35-29-23-17-11-5)72-98(143)170-114-100(126-94(139)71-83(65-59-53-47-41-34-28-22-16-10-4)165-95(140)67-61-55-49-43-36-30-24-18-12-6)117(163-79-91-102(145)113(169-97(142)70-82(132)64-58-52-46-40-33-27-21-15-9-3)99(118(167-91)180-183(160,161)162)125-93(138)69-81(131)63-57-51-45-39-32-26-20-14-8-2)168-92(112(114)178-181(154,155)156)80-164-123(121(150)151)74-90(175-124(122(152)153)73-85(133)101(144)108(176-124)87(135)76-128)111(110(177-123)89(137)78-130)173-120-106(149)115(105(148)107(171-120)86(134)75-127)174-119-104(147)103(146)116(179-182(157,158)159)109(172-119)88(136)77-129/h81-92,99-120,127-137,144-149H,7-80H2,1-6H3,(H,125,138)(H,126,139)(H,150,151)(H,152,153)(H2,154,155,156)(H2,157,158,159)(H2,160,161,162)/p-8/t81-,82-,83-,84-,85?,86+,87?,88+,89-,90-,91-,92-,99-,100-,101?,102-,103-,104+,105-,106+,107?,108?,109?,110-,111-,112-,113-,114-,115+,116+,117-,118-,119?,120?,123-,124?/m1/s1 XNYUHCDJIRFEJF-LIOVHSHWSA-F Cytosol Membrane logp 3.58 ALOGPS logs -4.18 ALOGPS solubility 1.87e-01 g/l ALOGPS logp 17.72 ChemAxon pka_strongest_acidic 0.38 ChemAxon iupac (2R,4R,5R,6R)-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-{[(3S,4S,5R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4R,5S)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylate ChemAxon average_mass 2694.9679 ChemAxon mono_mass 2693.366504142 ChemAxon smiles [H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO[C@@]3(C[C@@]([H])(OC4(CC([H])(O)C([H])(O)C([H])(O4)C([H])(O)CO)C([O-])=O)[C@@]([H])(OC4([H])OC([H])([C@@]([H])(O)CO)[C@@]([H])(O)[C@]([H])(OC5([H])OC([H])([C@@]([H])(O)CO)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(O)[C@]5([H])O)[C@]4([H])O)[C@]([H])(O3)[C@]([H])(O)CO)C([O-])=O)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC ChemAxon formula C124H219N2O54P3 ChemAxon inchi InChI=1S/C124H227N2O54P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(141)166-84(66-60-54-48-42-35-29-23-17-11-5)72-98(143)170-114-100(126-94(139)71-83(65-59-53-47-41-34-28-22-16-10-4)165-95(140)67-61-55-49-43-36-30-24-18-12-6)117(163-79-91-102(145)113(169-97(142)70-82(132)64-58-52-46-40-33-27-21-15-9-3)99(118(167-91)180-183(160,161)162)125-93(138)69-81(131)63-57-51-45-39-32-26-20-14-8-2)168-92(112(114)178-181(154,155)156)80-164-123(121(150)151)74-90(175-124(122(152)153)73-85(133)101(144)108(176-124)87(135)76-128)111(110(177-123)89(137)78-130)173-120-106(149)115(105(148)107(171-120)86(134)75-127)174-119-104(147)103(146)116(179-182(157,158)159)109(172-119)88(136)77-129/h81-92,99-120,127-137,144-149H,7-80H2,1-6H3,(H,125,138)(H,126,139)(H,150,151)(H,152,153)(H2,154,155,156)(H2,157,158,159)(H2,160,161,162)/p-8/t81-,82-,83-,84-,85?,86+,87?,88+,89-,90-,91-,92-,99-,100-,101?,102-,103-,104+,105-,106+,107?,108?,109?,110-,111-,112-,113-,114-,115+,116+,117-,118-,119?,120?,123-,124?/m1/s1 ChemAxon inchikey XNYUHCDJIRFEJF-LIOVHSHWSA-F ChemAxon polar_surface_area 913.34 ChemAxon refractivity 690.55 ChemAxon polarizability 288.41 ChemAxon rotatable_bond_count 108 ChemAxon acceptor_count 49 ChemAxon donor_count 19 ChemAxon physiological_charge -7 ChemAxon formal_charge -8 ChemAxon 46173154 CPD0-2240 Lipopolysaccharide core heptosyltransferase rfaQ P25742 RFAQ_ECOLI rfaQ http://ecmdb.ca/proteins/P25742.xml Lipopolysaccharide core heptose(I) kinase rfaP P25741 RFAP_ECOLI rfaP http://ecmdb.ca/proteins/P25741.xml Adenosine triphosphate + heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + Phospho-heptosyl-heptosyl-kdo2-lipidA ADP-L-Glycero-D-manno-heptose + Phospho-heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA