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Record Information
Version	2.0
Creation Date	2012-05-31 14:58:23 -0600
Update Date	2015-06-03 17:20:37 -0600
Secondary Accession Numbers	ECMDB21098
Identification
Name:	Lipid A
Description	Lipid A is a lipid that comprises the innermost of the three regions of the lipopolysaccharide (LPS) molecule found in the outer membrane of Gram-negative bacteria such as E. coli. Its hydrophobic nature allows it to anchor the LPS to the outer membrane. Lipid A consists of two glucosamine (carbohydrate/sugar) units with attached acyl chains ("fatty acids"), and normally containing one phosphate group on each carbohydrate. The E. coli lipid A typically has four C14 hydroxy acyl chains attached to the sugars and one C14 and one C12 attached to the beta hydroxy groups. (Wikipedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa16da078> Close
Synonyms:	Diphosphoryl hexaacyl lipid A NULL Synthetic E. coli lipid A
Chemical Formula:	C94H178N2O25P2
Weight:	Average: 1798.365 Monoisotopic: 1797.21939228
InChI Key:	GZQKNULLWNGMCW-PWQABINMSA-N
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
CAS number:	Not Available
IUPAC Name:	{[(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
Traditional IUPAC Name:	lipid A
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
Chemical Taxonomy
Description	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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Acylaminosugars
Alternative Parents	Saccharolipids Hexose phosphates Disaccharide phosphates N-acyl-alpha-hexosamines Tetracarboxylic acids and derivatives O-glycosyl compounds Beta hydroxy acids and derivatives Fatty acid esters Monoalkyl phosphates Oxanes N-acyl amines Secondary alcohols Secondary carboxylic acid amides Carboxylic acid esters Acetals Oxacyclic compounds Organic oxides Primary alcohols Carbonyl compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds
Substituents	Acylaminosugar Saccharolipid Hexose phosphate Disaccharide phosphate N-acyl-alpha-hexosamine Tetracarboxylic acid or derivatives Disaccharide Glycosyl compound O-glycosyl compound Monoalkyl phosphate Beta-hydroxy acid Fatty acid ester Alkyl phosphate Fatty acyl Phosphoric acid ester Oxane Organic phosphoric acid derivative N-acyl-amine Hydroxy acid Fatty amide Secondary carboxylic acid amide Secondary alcohol Carboxamide group Carboxylic acid ester Oxacycle Organoheterocyclic compound Carboxylic acid derivative Acetal Hydrocarbon derivative Primary alcohol Alcohol Carbonyl group Organonitrogen compound Organopnictogen compound Organic oxide Organic nitrogen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	laurate ester (CHEBI:47040 ) lipid As (CHEBI:47040 )
Physical Properties
State:	Solid
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0012 g/L ALOGPS logP 6.8 ALOGPS logP 23.97 ChemAxon logS -6.2 ALOGPS pKa (Strongest Acidic) 0.61 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 405.53 Ų ChemAxon Rotatable Bond Count 88 ChemAxon Refractivity 477.18 m³·mol⁻¹ ChemAxon Polarizability 213.02 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:	superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0089-0123161900-a0b29cb2a5620669c282 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ff1-1223093400-c7c1cee9a9256bd28b6e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00e9-0242489600-77966b68d48be8286cb4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002b-9510133200-a35ef4a869747eee82f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9010121101-806a5bc007a2af4acfae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-0c15069faff9658a6001 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004j-1290020200-6ff62fce7a1fc5f77865 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-056r-4390030000-fc40ff09fa4e7b1694bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-056v-9640124000-40187fa65042441659ca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0ul1-0001090300-7844b0b3a9cc31e69e69 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0kor-3740180900-796c703855f3e6dcf409 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-4910012000-0ea888969ae27836334e View in MoNA
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 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. Pubmed: 21097882 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 47040 HMDB ID HMDB13244 Pubchem Compound ID 9877306 Kegg ID C13908 ChemSpider ID 8052983 Wikipedia Lipid A BioCyc ID Lipid-A EcoCyc ID Lipid-A

Enzymes

Transporters