galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate (ECMDB24225) (M2MDB006342)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:50:14 -0600
Update Date2016-09-13 16:35:45 -0600
Secondary Accession Numbers
  • ECMDB24225
Identification
Name:galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate
DescriptionGalactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate is an intermediate in lipid A-core biosynthesis pathway in E.coli. It is a substrate for the enzyme UDP-D-glucose:(glucosyl)LPS alpha-1,3-glucosyltransferase which catalyzes the reaction UDP-alpha-D-glucose + galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate -> galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP + H+. It is also a product for enzyme UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase which catalyzes reaction UDP-alpha-D-galactose + glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate -> galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP + H+ (BioCyc compound: CPD0-936).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Galactosyl-glucosyl-(heptosyl)3-kdo2-lipid a-bisphosphoric acid
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-{[(2S,3S,4R,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4R,5R,6R)-6-[(1S)-2-{[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3-hydroxy-5-(phosphonatooxy)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-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-{[(2S,3S,4R,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4R,5R,6R)-6-[(1S)-2-{[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3-hydroxy-5-(phosphonatooxy)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-10
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.75 g/LALOGPS
logP2.42ALOGPS
logP10.01ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.14ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count65ChemAxon
Hydrogen Donor Count28ChemAxon
Polar Surface Area1216.23 ŲChemAxon
Rotatable Bond Count120ChemAxon
Refractivity777.99 m³·mol⁻¹ChemAxon
Polarizability341.02 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-α-D-galactose > galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + Uridine 5'-diphosphate + Hydrogen ion
galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID51351793
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lipopolysaccharide 1,6-galactosyltransferase
General function:
Involved in biosynthetic process
Specific function:
Adds a galactose goup to a glucose group of LPS
Gene Name:
rfaB
Uniprot ID:
P27127
Molecular weight:
40826
Protein Details
2. Lipopolysaccharide 1,3-galactosyltransferase
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
UDP-galactose + lipopolysaccharide = UDP + 3- alpha-D-galactosyl-[lipopolysaccharide glucose]
Gene Name:
rfaI
Uniprot ID:
P27128
Molecular weight:
39423
Reactions
UDP-galactose + lipopolysaccharide = UDP + 3-alpha-D-galactosyl-[lipopolysaccharide glucose].