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UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine (M2MDB006332)

Record Information
Version2.0
Creation Date2015-09-08 17:50:07 -0600
Update Date2016-09-13 16:35:44 -0600
Secondary Accession Numbers
  • ECMDB24215
Identification
Name:UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine
DescriptionUDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine is an intermediate in lipid IVA biosynthesis pathway in E.coli. It is a substrate for the enzymes UDP-3-O-acyl-N-acetylglucosamine deacetylase which catalyzes the reaction UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O -> UDP-3-O-(3-hydroxymyristoyl)-alpha-D-glucosamine + acetate. It is also a product for enzyme UDP-N-acetylglucosamine acyltransferase which catalyzes reaction a (3R)-3-hydroxymyristoyl-[acp] + UDP-N-acetyl-alpha-D-glucosamine -> UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + a holo-[acyl-carrier protein] (BioCyc compound: UDP-OHMYR-ACETYLGLUCOSAMINE).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamineChEBI
UDP-3-O-(3-Hydroxytetradecanoyl)-N-acetylglucosamineChEBI
UDP-3-O-[(3R)-3-Hydroxymyristoyl]-N-acetylglucosamineChEBI
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-N-acetyl-alpha-D-glucosamineChEBI
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-N-acetylglucosamine dianionChEBI
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-N-acetyl-a-D-glucosamineGenerator
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-N-acetyl-α-D-glucosamineGenerator
UDP-3-HMAGlcMeSH
Chemical Formula:
Weight:Average: Not Available
Monoisotopic: Not Available
InChI Key:Not Available
InChI:Not Available
CAS number:Not Available
IUPAC Name:N-[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanecarboximidate
Traditional IUPAC Name:N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanecarboximidate
SMILES:Not Available
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Saccharolipid
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Fatty acid ester
  • Pyrimidone
  • Oxane
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Phosphoric acid ester
  • Monosaccharide
  • Hydroxy acid
  • Pyrimidine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Acetamide
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.74 g/LALOGPS
logP1.15ALOGPS
logP0.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area339.35 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity205.41 m³·mol⁻¹ChemAxon
Polarizability79.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Uridine diphosphate-N-acetylglucosamine + (3R)-3-hydroxymyristoyl-[acp] > a holo-[acyl-carrier protein] + UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine + Water > Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
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 ID61494
HMDB IDNot Available
Pubchem Compound ID25244942
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Acyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferase
General function:
Involved in transferase activity
Specific function:
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell
Gene Name:
lpxA
Uniprot ID:
P0A722
Molecular weight:
28080
Reactions
(R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] + UDP-N-acetylglucosamine = [acyl-carrier-protein] + UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine.
Protein Details
2. UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase
General function:
Involved in UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase activity
Specific function:
The key enzyme in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell. Degraded by FtsH; when the activity of FtsH is reduced too much lipid A and not enough phospholipids are made (both pathways use the same precursor), which is lethal
Gene Name:
lpxC
Uniprot ID:
P0A725
Molecular weight:
33956
Reactions
UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine + H(2)O = UDP-3-O-(3-hydroxytetradecanoyl)-glucosamine + acetate.