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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:09 -0600
Update Date	2016-09-13 16:35:45 -0600
Secondary Accession Numbers	ECMDB24220
Identification
Name:	glucosyl-(heptosyl)2-Kdo2-lipid A
Description	Glucosyl-(heptosyl)2-Kdo2-lipid A is an intermediate in lipid A-core biosynthesis pathway in E.coli. It is a substrate for the enzyme lipopolysaccharide core heptose (I) kinase which catalyzes the reaction glucosyl-(heptosyl)2-Kdo2-lipid A + ATP -> glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP + H+. It is also a product for enzyme lipopolysaccharide glucosyltransferase I which catalyzes reaction UDP-alpha-D-glucose + (heptosyl)2-Kdo2-lipid A -> glucosyl-(heptosyl)2-Kdo2-lipid A + UDP + H+ (BioCyc compound: CPD0-932).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9438c784> Close
Synonyms:	Value Source D-GLC-(1->3)-L-alpha-D-hep-(1->3)-L-alpha-D-hep-(1->5)-[alpha-kdo-(2->4)]-alpha-kdo-(2->6)-lipid a hexaanion ChEBI D-GLC-(1->3)-L-alpha-D-hep-(1->3)-L-alpha-D-hep-(1->5)-[alpha-kdo-(2->4)]-alpha-kdo-(2->6)-lipid a(6-) ChEBI Glucosyl-(heptosyl)2-(kdo)2-lipid a ChEBI Glucosyl-(heptosyl)2-(kdo)2-lipid a hexaanion ChEBI
Chemical Formula:
Weight:	Average: Not Available Monoisotopic: Not Available
InChI Key:	Not Available
InChI:	Not Available
CAS number:	Not Available
IUPAC Name:	(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-5-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-{[(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-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
Traditional IUPAC Name:	(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-5-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-{[(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-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
SMILES:	Not Available
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 Hexacarboxylic acids and derivatives Saccharolipids Hexose phosphates N-acyl-alpha-hexosamines C-glucuronides Alkyl glycosides C-glycosyl compounds O-glycosyl compounds Beta hydroxy acids and derivatives Fatty acid esters Ketals Alkyl phosphates Pyrans Oxanes N-acyl amines Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters Carboxylic acid salts Carboxylic acids Polyols Oxacyclic compounds Organopnictogen compounds Primary alcohols Carbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Oligosaccharide phosphate Oligosaccharide Hexacarboxylic acid or derivatives Acylaminosugar Saccharolipid Hexose phosphate N-acyl-alpha-hexosamine Fatty acyl glycoside C-glucuronide Alkyl glycoside O-glycosyl compound C-glycosyl compound Glycosyl compound Fatty acid ester Ketal Beta-hydroxy acid Pyran Fatty acyl Phosphoric acid ester Oxane Hydroxy acid Organic phosphoric acid derivative N-acyl-amine Fatty amide Alkyl phosphate Carboxamide group Carboxylic acid ester Carboxylic acid salt Secondary carboxylic acid amide Secondary alcohol Organoheterocyclic compound Carboxylic acid Carboxylic acid derivative Acetal Oxacycle Polyol Alcohol Organic nitrogen compound Carbonyl group Hydrocarbon derivative Organic oxide Organopnictogen compound Primary alcohol Organonitrogen compound Organic anion Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	lipid A oxoanion (CHEBI:61997 )
Physical Properties
State:	Not Available
Charge:	-6
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.2 g/L ALOGPS logP 3.09 ALOGPS logP 14.43 ChemAxon logS -4.2 ALOGPS pKa (Strongest Acidic) 0.6 ChemAxon Physiological Charge -6 ChemAxon Hydrogen Acceptor Count 50 ChemAxon Hydrogen Donor Count 23 ChemAxon Polar Surface Area 933.32 Ų ChemAxon Rotatable Bond Count 109 ChemAxon Refractivity 689.95 m³·mol⁻¹ ChemAxon Polarizability 297.36 ų ChemAxon Number of Rings 7 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:	(heptosyl)2-Kdo2-lipid A + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A glucosyl-(heptosyl)2-Kdo2-lipid A + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831 lipopolysaccharide biosynthesis II PW001905 lipopolysaccharide biosynthesis III PW002059
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Not Available
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 51351771 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes