UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine (PAMDB000644)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000644
Identification
Name: UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
Description:UDP-3-o-(3-hydroxymyristoyl)-n-acetylglucosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine
  • UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine
  • UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
  • UDP-3-O-(3-Hydroxytetradecanoyl)-N-acetylglucosamine
  • UDP-HMyrGlcNAc
  • UDP-Ohmyr-acetylglucosamine
Chemical Formula: C31H53N3O19P2
Average Molecular Weight: 833.7087
Monoisotopic Molecular Weight: 833.274849553
InChI Key: TZSJGZGYQDNRRX-MPLCHSTDSA-N
InChI:InChI=1S/C31H53N3O19P2/c1-3-4-5-6-7-8-9-10-11-12-19(37)15-23(39)51-28-24(32-18(2)36)30(50-20(16-35)26(28)41)52-55(46,47)53-54(44,45)48-17-21-25(40)27(42)29(49-21)34-14-13-22(38)33-31(34)43/h13-14,19-21,24-30,35,37,40-42H,3-12,15-17H2,1-2H3,(H,32,36)(H,44,45)(H,46,47)(H,33,38,43)/t19-,20-,21-,24-,25-,26-,27-,28-,29-,30-/m1/s1
CAS number: 108636-29-9
IUPAC Name:N-[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-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]ethanimidic acid
Traditional IUPAC Name: N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-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]ethanimidic acid
SMILES:[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.33 mg/mLALOGPS
logP0.82ALOGPS
logP0.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area333.69 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity184.31 m3·mol-1ChemAxon
Polarizability80.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
(R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Uridine diphosphate-N-acetylglucosamine <> acyl carrier protein + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
Water + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine <> Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Uridine diphosphate-N-acetylglucosamine + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] <> Acyl-carrier protein + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Acyl-carrier protein
(R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] + Uridine diphosphate-N-acetylglucosamine > [acyl-carrier-protein] + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910000020-fedcabb1e352348e4b41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910010000-9c7cdad9942cd448b2e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3910000000-1906defd57b0d60b4180View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-7912501340-ee6a700cf210afdb6a69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-8915131020-7c28b07f154e3dacae45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5922000000-e1498ccc14935f8be289View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28131
HMDB IDNot Available
Pubchem Compound ID25244942
Kegg IDC04738
ChemSpider ID26332242
Wikipedia IDNot Available
BioCyc IDUDP-OHMYR-ACETYLGLUCOSAMINE
EcoCyc IDUDP-OHMYR-ACETYLGLUCOSAMINE
Ligand ExpoU20

Enzymes

Protein Details
• 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
Locus Tag:
PA3644
Molecular weight:
28 kDa
Reactions
(R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] + UDP-N-acetylglucosamine = [acyl-carrier-protein] + UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine.
Protein Details
• 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
Locus Tag:
PA4406
Molecular weight:
33.4 kDa
Reactions
UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine + H(2)O = UDP-3-O-(3-hydroxytetradecanoyl)-glucosamine + acetate.
Protein Details
• Acyl carrier protein
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa