2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate (ECMDB24217) (M2MDB006334)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:50:07 -0600
Update Date2016-09-13 16:35:44 -0600
Secondary Accession Numbers
  • ECMDB24217
Identification
Name:2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
Description2,3-bis((3R)-3-Hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in E. coli had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of E. coli.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphoric acid
Chemical Formula:
Weight:Average: Not Available
Monoisotopic: Not Available
InChI Key:Not Available
InChI:Not Available
CAS number:Not Available
IUPAC Name:5-hydroxy-6-(hydroxymethyl)-3-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl phosphate
Traditional IUPAC Name:5-hydroxy-6-(hydroxymethyl)-3-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl phosphate
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
  • N-acyl-alpha-hexosamine
  • Monosaccharide phosphate
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty amide
  • Hydroxy acid
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP4.85ALOGPS
logP5.82ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.17ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area217.97 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity178.31 m³·mol⁻¹ChemAxon
Polarizability80.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate)
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 ID74413591
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lipid-A-disaccharide synthase
General function:
Involved in lipid-A-disaccharide synthase activity
Specific function:
Condensation of UDP-2,3-diacylglucosamine and 2,3- diacylglucosamine-1-phosphate to form lipid A disaccharide, a precursor of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell
Gene Name:
lpxB
Uniprot ID:
P10441
Molecular weight:
42382
Reactions
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate = UDP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate.
Protein Details
2. UDP-2,3-diacylglucosamine hydrolase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of the pyrophosphate bond of UDP-2,3-diacylglucosamine to yield 2,3-diacylglucosamine 1- phosphate (lipid X) and UMP
Gene Name:
lpxH
Uniprot ID:
P43341
Molecular weight:
26894
Reactions
UDP-2,3-bis((3R)-3-hydroxymyristoyl)-alpha-D-glucosamine + H(2)O = 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate + UMP.