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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:04 -0600
Update Date	2015-06-03 17:20:57 -0600
Secondary Accession Numbers	ECMDB21234
Identification
Name:	KDO(2)-lipid IV(A) with laurate
Description	KDO(2)-lipid IV(a) is a saccharolipid. The most familiar saccharolipids are the acylated glucosamine precursors of the lipid A component of the lipopolysaccharides in Gram-negative bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in E. coli is Kdo2-Lipid A, a hexa-acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab86490c> Close
Synonyms:	kdo(2)-Lipid iv(a) with laate kdo(2)-Lipid iv(a) with laic acid KDO(2)-lipid IV(A) with lauric acid KDO2-(lauroyl)-lipid IVA
Chemical Formula:	C96H170N2O38P2
Weight:	Average: 2022.3151 Monoisotopic: 2021.09068211
InChI Key:	JVUUYJGQIVCMIU-ZODGSCPMSA-H
InChI:	InChI=1S/C96H176N2O38P2/c1-6-11-16-21-26-31-36-41-46-51-66(101)56-76(107)97-81-89(130-79(110)57-67(102)52-47-42-37-32-27-22-17-12-7-2)85(114)74(128-92(81)136-138(122,123)124)64-125-91-82(98-77(108)59-69(54-49-44-39-34-29-24-19-14-9-4)127-78(109)55-50-45-40-35-30-25-20-15-10-5)90(131-80(111)58-68(103)53-48-43-38-33-28-23-18-13-8-3)88(135-137(119,120)121)75(129-91)65-126-95(93(115)116)61-73(84(113)87(133-95)72(106)63-100)132-96(94(117)118)60-70(104)83(112)86(134-96)71(105)62-99/h66-75,81-92,99-106,112-114H,6-65H2,1-5H3,(H,97,107)(H,98,108)(H,115,116)(H,117,118)(H2,119,120,121)(H2,122,123,124)/p-6/t66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,95-,96-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-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}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonatooxy)oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylate
Traditional IUPAC Name:	(2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-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}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonatooxy)oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylate
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])(O[C@@]4(C[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O4)[C@]([H])(O)CO)C([O-])=O)[C@@]([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])(O)CCCCCCCCCCC)[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
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	Oligosaccharide phosphates Saccharolipids Hexose phosphates Pentacarboxylic acids and derivatives N-acyl-alpha-hexosamines C-glucuronides O-glycosyl compounds C-glycosyl compounds Ketals Fatty acid esters Beta hydroxy acids and derivatives Alkyl phosphates Pyrans N-acyl amines Oxanes Carboxylic acid esters Secondary carboxylic acid amides Secondary alcohols Oxacyclic compounds Carboxylic acids Primary alcohols Organic oxides Carbonyl compounds Organonitrogen compounds Organopnictogen compounds Hydrocarbon derivatives Organic anions
Substituents	Oligosaccharide phosphate Oligosaccharide Acylaminosugar Saccharolipid Hexose phosphate Pentacarboxylic acid or derivatives N-acyl-alpha-hexosamine C-glucuronide C-glycosyl compound Glycosyl compound O-glycosyl compound Beta-hydroxy acid Ketal Fatty acid ester Fatty amide Fatty acyl Hydroxy acid N-acyl-amine Alkyl phosphate Organic phosphoric acid derivative Oxane Pyran Phosphoric acid ester Carboxamide group Secondary alcohol Secondary carboxylic acid amide Carboxylic acid ester Carboxylic acid derivative Organoheterocyclic compound Carboxylic acid Oxacycle Acetal Primary alcohol Organopnictogen compound Alcohol Organic oxide Carbonyl group Hydrocarbon derivative Organonitrogen compound Organic nitrogen compound Organic anion Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	lipid A oxoanion (CHEBI:61524 )
Physical Properties
State:	Not Available
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.061 g/L ALOGPS logP 4.37 ALOGPS logP 16.61 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 0.55 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 35 ChemAxon Hydrogen Donor Count 13 ChemAxon Polar Surface Area 656.32 Ų ChemAxon Rotatable Bond Count 84 ChemAxon Refractivity 540.78 m³·mol⁻¹ ChemAxon Polarizability 220.47 ų ChemAxon Number of Rings 4 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:	Dodecanoyl-ACP (n-C12:0ACP) + KDO(2)-lipid IV(A) > acyl carrier protein + KDO(2)-lipid IV(A) with laurate KDO(2)-lipid IV(A) with laurate + Myristoyl-ACP (n-C14:0ACP) > acyl carrier protein + KDO2-Lipid A
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:	superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Not Available
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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 61524 HMDB ID Not Available Pubchem Compound ID 25244565 Kegg ID Not Available ChemSpider ID 26332260 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes