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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:07 -0600
Update Date	2016-09-13 16:35:44 -0600
Secondary Accession Numbers	ECMDB24217
Identification
Name:	2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
Description	2,3-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa71d4744> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Acylaminosugars
Alternative Parents	Saccharolipids N-acyl-alpha-hexosamines Monosaccharide phosphates Beta hydroxy acids and derivatives Fatty acid esters Alkyl phosphates Oxanes N-acyl amines Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Hydrocarbon derivatives Organic oxides Organonitrogen compounds Carbonyl compounds Organopnictogen compounds Organic anions
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 Framework	Aliphatic heteromonocyclic compounds
External Descriptors	a small molecule (BISOHMYR-GLUCOSAMINYL-1P )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0046 g/L ALOGPS logP 4.85 ALOGPS logP 5.82 ChemAxon logS -5.2 ALOGPS pKa (Strongest Acidic) 1.17 ChemAxon pKa (Strongest Basic) -1.6 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 217.97 Ų ChemAxon Rotatable Bond Count 30 ChemAxon Refractivity 178.31 m³·mol⁻¹ ChemAxon Polarizability 80.25 ų ChemAxon Number of Rings 1 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:	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 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 74413591 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes