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UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine (M2MDB003524)

Record Information
Version2.0
Creation Date2012-10-10 12:18:13 -0600
Update Date2015-06-03 17:26:00 -0600
Secondary Accession Numbers
  • ECMDB23134
Identification
Name:UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine
DescriptionUDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine is an intermediate in Lipid IVA synthesis. It is a substrate for the enzyme UDP-2,3-diacylglucosamine diphosphatase which catalyzes the reaction UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + H2O = 2,3-bis[(3R)-3-hydroxymyristoyl]-beta-D-glucosaminyl 1-phosphate + UMP.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • OH-MYRISTOYL
  • UDP-2,3-bis(3-hydroxymyristoyl)glucosamine
  • UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine
  • UDP-2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosamine
  • UDP-2,3-bis(3R)-3-hydroxymyristoyl-alpha-D-glucosamine
  • UDP-2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosamine
  • UDP-2,3-Bis(O-(3R)-3-hydroxymyristoyl)-a-D-glucosamine
  • UDP-2,3-Bis(O-(3R)-3-hydroxymyristoyl)-α-D-glucosamine
  • UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-a-D-glucosamine
  • UDP-2,3-bisO-(3R)-3-hydroxymyristoyl-alpha-D-glucosamine
  • UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-α-D-glucosamine
  • UDP-2,3-diacyl-glucosamine
Chemical Formula:C43H75N3O20P2
Weight:Average: 1016.0112
Monoisotopic: 1015.441914879
InChI Key:KOJCFMYSTWNMQW-RUAJDYCTSA-L
InChI:InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/p-2/t29-,30-,31-,32-,36-,37-,38-,39-,40-,41-,42-/m1/s1
CAS number:Not Available
IUPAC Name:(3R)-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]-3-hydroxytetradecanecarboximidate
Traditional IUPAC Name:(3R)-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]-3-hydroxytetradecanecarboximidate
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([O-])C[C@]([H])(O)CCCCCCCCCCC
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
  • Acylaminosugar
  • Saccharolipid
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Fatty acid ester
  • Pyrimidone
  • Fatty amide
  • Hydropyrimidine
  • Hydroxy acid
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Fatty acyl
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Urea
  • Lactam
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • 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 Solubility0.65 g/LALOGPS
logP3.32ALOGPS
logP5.06ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area359.58 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity262.16 m³·mol⁻¹ChemAxon
Polarizability105.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] + UDP-3-O-((3R)-hydroxymyristoyl)-alpha-D-glucosamine > UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine + a holo-[acyl-carrier-protein]
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-9100000000-ff037811dffd71bb2f75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-6420000009-b8b6523908978fb04445View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-5910001002-3e3c925ae584f1e111e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000001-1a49ddada35d93c31506View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9430010000-507653e03e5b6557f747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0037-9441000000-773a819aef4b199daa61View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID78847
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. UDP-3-O-[3-hydroxymyristoyl] glucosamine N-acyltransferase
General function:
Involved in transferase activity
Specific function:
UDP-3-O-(3-hydroxytetradecanoyl)glucosamine + (R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] = UDP-2,3-bis(3- hydroxytetradecanoyl)glucosamine + [acyl-carrier-protein]
Gene Name:
lpxD
Uniprot ID:
P21645
Molecular weight:
36038
Reactions
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] + UDP-3-O-((3R)-hydroxymyristoyl)-alpha-D-glucosamine = UDP-2,3-bis(O-(3R)-3-hydroxymyristoyl)-alpha-D-glucosamine + a holo-[acyl-carrier-protein].