2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (PAMDB000903)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000903
Identification
Name: 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Description:2,3-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 Pseudomonas aeruginosa 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 711.8611
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as saccharolipids. These are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Saccharolipids
Sub ClassNot Available
Direct Parent Saccharolipids
Alternative Parents
Substituents
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Amino saccharide
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • 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
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0088 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count30ChemAxon
Refractivity181.08 m3·mol-1ChemAxon
Polarizability79.77 Å3ChemAxon
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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