2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (ECMDB20054) (M2MDB000903)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (371)
Record Information
Version2.0
Creation Date2012-05-31 14:25:03 -0600
Update Date2015-06-03 17:19:13 -0600
Secondary Accession Numbers
  • ECMDB20054
Identification
Name:2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Description2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Lipid X is a diacylglucosamine 1-phosphate bearing beta-hydroxymyristoyl groups at positions 2 and 3. (PMID 2998869) The simplest of these, lipid X, is a derivative of glucosamine-1-phosphate substituted with beta-hydroxymyristoyl moieties at positions 2 and 3. (PMID 6382553) Lipid X (2,3-diacylglucosamine-1-phosphate) is a novel monosaccharide precursor of lipid A that has some of the physiologic activities of endotoxin but little toxicity. Perhaps because lipid X is a subunit of lipid A, lipid X shows a partial pyrogenic effect while also decreasing the pyrogenic activity of complete lipopolysaccharide (LPS). Lipid X is a potential prototype compound for a new type of chemotherapy directed at blocking the harmful effects of LPS during bacterial septicemia. (PMID 3308707) A monosaccharide precursor of Escherichia coli lipid A, designated lipid X, which is a diacylglucosamine 1-phosphate with beta-hydroxymyristoyl groups at positions 2 and 3, was shown to have the ability to induce the production of tumor necrosis factor (TNF)-like tumor-cytotoxic factor by a murine macrophage-like cell line, J774. (PMID 3701065)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3-bis(β-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(β-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(b-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(b-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(beta-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(beta-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(β-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(β-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • BHMyrGc1P
  • Lipid x
  • Monosaccharide precursor, e coli lipid a
Chemical Formula:C34H66NO12P
Weight:Average: 711.8611
Monoisotopic: 711.432263093
InChI Key:HEHQDWUWJVPREQ-JIMHHRIFSA-N
InChI:InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26?,27?,28-,31-,32-,33-,34-/m1/s1
CAS number:Not Available
IUPAC Name:3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]tetradecanimidic acid
Traditional IUPAC Name:3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]tetradecanimidic acid
SMILES:[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Aryl alkyl ketone
  • Gamma-keto acid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Keto acid
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0088 g/LALOGPS
logP4.52ALOGPS
logP5.83ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)1.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.8 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity181.08 m³·mol⁻¹ChemAxon
Polarizability79.77 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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 + 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
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r6-0120609100-a3418a2ad4cddeb66441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-5351915000-2038544bb80f14ad6771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r3-2890715000-5af3f20eb30b89456fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9011121100-2ea4252c17dcdd92a277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010111000-fcbb16bf61e785c307ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6b54ac64344d43ed0e21View 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:
  • Amano, F., Nishijima, M., Akagawa, K., Akamatsu, Y. (1985). "Enhancement of O2- generation and tumoricidal activity of murine macrophages by a monosaccharide precursor of Escherichia coli lipid A." FEBS Lett 192:263-266. Pubmed: 2998869
  • Amano, F., Nishijima, M., Akamatsu, Y. (1986). "A monosaccharide precursor of Escherichia coli lipid A has the ability to induce tumor-cytotoxic factor production by a murine macrophage-like cell line, J774.1." J Immunol 136:4122-4127. Pubmed: 3701065
  • Golenbock, D. T., Will, J. A., Raetz, C. R., Proctor, R. A. (1987). "Lipid X ameliorates pulmonary hypertension and protects sheep from death due to endotoxin." Infect Immun 55:2471-2476. Pubmed: 3308707
  • 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
  • Raetz, C. R. (1984). "The enzymatic synthesis of lipid A: molecular structure and biologic function of monosaccharide precursors." Rev Infect Dis 6:463-471. Pubmed: 6382553
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16942
HMDB IDNot Available
Pubchem Compound ID10078514
Kegg IDC04824
ChemSpider ID8254052
Wikipedia IDNot Available
BioCyc IDBISOHMYR-GLUCOSAMINYL-1P
EcoCyc IDBISOHMYR-GLUCOSAMINYL-1P

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-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.