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alpha-Kdo-(2→6)-lipid IVA (M2MDB006335)

Record Information
Version2.0
Creation Date2015-09-08 17:50:08 -0600
Update Date2016-09-13 16:35:44 -0600
Secondary Accession Numbers
  • ECMDB24218
Identification
Name:alpha-Kdo-(2→6)-lipid IVA
Descriptionalpha-Kdo-(2→6)-lipid IVA is an intermediate in Kdo transfer to lipid IVA I pathway in E.coli. It is a substrate for the enzyme KDO transferase which catalyzes the reaction alpha-Kdo-(2→6)-lipid IVA + CMP-3-deoxy-alpha-D-manno-octulosonate -> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA + CMP + H+. It is also a product for enzyme 3-deoxy-D-manno-octulosonic acid transferase which catalyzes reaction CMP-3-deoxy-alpha-D-manno-octulosonate + lipid IVA -> alpha-Kdo-(2→6)-lipid IVA + CMP + H+ (BioCyc compound: KDO-LIPID-IVA).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • a-kdo-(2→6)-lipid iva
  • α-kdo-(2→6)-lipid iva
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)-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonatooxy)oxan-2-yl]methoxy}-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonatooxy)oxan-2-yl]methoxy}oxane-2-carboxylate
Traditional IUPAC Name:(kdo)-lipid iva(5-)
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
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Ketal
  • Fatty acid ester
  • Fatty acyl
  • Fatty amide
  • Alkyl phosphate
  • Hydroxy acid
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP4.26ALOGPS
logP11.31ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)0.6ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area523.99 ŲChemAxon
Rotatable Bond Count67ChemAxon
Refractivity407.16 m³·mol⁻¹ChemAxon
Polarizability176.8 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
CMP-3-Deoxy-D-manno-octulosonate + (2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) > Cytidine monophosphate + Hydrogen ion + alpha-Kdo-(2→6)-lipid IVA + Cytidine monophosphate
alpha-Kdo-(2→6)-lipid IVA + CMP-3-Deoxy-D-manno-octulosonate > Cytidine monophosphate + Hydrogen ion + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + Cytidine monophosphate + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA
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 ID60364
HMDB IDNot Available
Pubchem Compound ID25246208
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-deoxy-D-manno-octulosonic-acid transferase
General function:
Involved in biosynthetic process
Specific function:
Essential step in lipopolysaccharides biosynthesis. Acts at transfer of 3-deoxy-D-mono octulonic acid (KDO) from CMP-KDO to a tetraacyldisaccharide 1,4'-bisphosphate precursor of lipid A (lipid IVA). Transfers two molecules of KDO to lipid IVA. Degraded by FtsH; therefore FtsH regulates the addition of the sugar moiety of the LPS and thus the maturation of the LPS precursor
Gene Name:
waaA
Uniprot ID:
P0AC75
Molecular weight:
47291