UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine (ECMDB20201) (M2MDB001047)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (627)
Record Information
Version2.0
Creation Date2012-05-31 14:32:51 -0600
Update Date2015-06-03 17:19:31 -0600
Secondary Accession Numbers
  • ECMDB20201
Identification
Name:UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
DescriptionUDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine is a member of the chemical class known as Sulfanylbenzoic Acid Derivatives. These are benzoic acid derivatives which bear a sulfanyl group (R-SH) attached to the benzene ring.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • UDP-2,3-Bis(3-hydroxymyristoyl)glucosamine
  • UDP-2,3-Bis(3-hydroxytetradecanoyl)-D-glucosamine
  • UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
  • UDP-2,3-Bis(b-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-Bis(beta-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-Bis(β-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosamine
  • UDP-2,3-Bis[(3r)-3-hydroxymyristoyl]-α-D-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-Diacyl-glucosamine
  • UDP-BHMyrGlc
Chemical Formula:C43H77N3O20P2
Weight:Average: 1018.0271
Monoisotopic: 1017.457564943
InChI Key:KOJCFMYSTWNMQW-RUAJDYCTSA-N
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)/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-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]-3-hydroxytetradecanimidic acid
Traditional IUPAC Name:(3R)-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]-3-hydroxytetradecanimidic 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(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
  • Monoalkyl phosphate
  • Pyrimidone
  • Fatty amide
  • Hydropyrimidine
  • Hydroxy acid
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Fatty acyl
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Urea
  • Lactam
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • 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 Solubility0.43 g/LALOGPS
logP2.66ALOGPS
logP5.06ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area353.92 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity241.06 m³·mol⁻¹ChemAxon
Polarizability105.54 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
(R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine > acyl carrier protein + Hydrogen ion + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <>2 Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Water <> Uridine 5'-monophosphate + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Acyl-carrier protein + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] <> UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Acyl-carrier protein
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate <> Uridine 5'-diphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine > Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine > Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate > Uridine 5'-diphosphate + 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2910000101-46860ca31ec971b6dd89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910001100-53f313794898ec8fecedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3910000100-1158711cf21b4e95e971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9822230205-2ea21d2ff53d2b4aa05bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vp-8912030614-d3d1eb5aea19bc3f5320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5912100000-acba712642beaf0be36eView 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:
  • 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
  • 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 ID17787
HMDB IDNot Available
Pubchem Compound ID2372447
Kegg IDC04652
ChemSpider ID1772247
Wikipedia IDNot Available
BioCyc IDOH-MYRISTOYL
EcoCyc IDOH-MYRISTOYL
Ligand ExpoUDG

Enzymes

Protein Details
1. CDP-diacylglycerol pyrophosphatase
General function:
Involved in CDP-diacylglycerol diphosphatase activity
Specific function:
CDP-diacylglycerol + H(2)O = CMP + phosphatidate
Gene Name:
cdh
Uniprot ID:
P06282
Molecular weight:
28451
Reactions
CDP-diacylglycerol + H(2)O = CMP + phosphatidate.
Protein Details
2. 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
3. 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].
Protein Details
4. 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.