1.0 2011-09-21 01:54:30 UTC 2017-04-03 05:02:20 UTC FDB029354 Lipid A Lipid A is a lipid component of an endotoxin held responsible for toxicity of Gram-negative bacteria. It is the innermost of the three regions of the lipopolysaccharide (LPS, also called endotoxin) molecule, and its hydrophobic nature allows it to anchor the LPS to the outer membrane. While its toxic effects can be damaging, the sensing of lipid A by the human immune system may also be critical for the onset of immune responses to Gram-negative infection, and for the subsequent successful fight against the infection.; Many of the immune activating abilities of LPS can be attributed to the lipid A unit. It is a very potent stimulant of the immune system, activating cells (for example, monocytes or macrophages) at picogram per milliliter quantities. [HMDB] Dioryl hexaacyl lipid a Diphosphoryl hexaacyl lipid A synthetic E. coli lipid A C94H178N2O25P2 1798.365 1797.21939228 {[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid lipid A 302-72-7 CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@H]1OP(O)(O)=O InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1 GZQKNULLWNGMCW-PWQABINMSA-N belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Acylaminosugars Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acid esters Disaccharide phosphates Fatty acid esters Hexose phosphates Hydrocarbon derivatives Monoalkyl phosphates N-acyl amines N-acyl-alpha-hexosamines O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Saccharolipids Secondary alcohols Secondary carboxylic acid amides Tetracarboxylic acids and derivatives Acetal Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Beta-hydroxy acid Carbonyl group Carboxamide group Carboxylic acid derivative Carboxylic acid ester Disaccharide Disaccharide phosphate Fatty acid ester Fatty acyl Fatty amide Glycosyl compound Hexose phosphate Hydrocarbon derivative Hydroxy acid Monoalkyl phosphate N-acyl-alpha-hexosamine N-acyl-amine O-glycosyl compound Organic nitrogen compound Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Primary alcohol Saccharolipid Secondary alcohol Secondary carboxylic acid amide Tetracarboxylic acid or derivatives laurate ester lipid As Solid logp 6.80 ALOGPS logs -6.17 ALOGPS solubility 1.21e-03 g/l ALOGPS logp 23.97 ChemAxon pka_strongest_acidic 0.61 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid ChemAxon average_mass 1798.365 ChemAxon mono_mass 1797.21939228 ChemAxon smiles CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@H]1OP(O)(O)=O ChemAxon formula C94H178N2O25P2 ChemAxon inchi InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1 ChemAxon inchikey GZQKNULLWNGMCW-PWQABINMSA-N ChemAxon polar_surface_area 405.53 ChemAxon refractivity 477.18 ChemAxon polarizability 213.02 ChemAxon rotatable_bond_count 88 ChemAxon acceptor_count 19 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 301225 Specdb::MsMs 301226 Specdb::MsMs 301227 Specdb::MsMs 343702 Specdb::MsMs 343703 Specdb::MsMs 343704 Specdb::MsMs 2436997 Specdb::MsMs 2436998 Specdb::MsMs 2436999 Specdb::MsMs 2528667 Specdb::MsMs 2528668 Specdb::MsMs 2528669 HMDB13244 47040