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2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (M2MDB003483)

Record Information
Version2.0
Creation Date2012-10-10 12:16:00 -0600
Update Date2015-06-03 17:25:54 -0600
Secondary Accession Numbers
  • ECMDB23093
Identification
Name:2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Description2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in LPS synthesis. It is a substrate for the protein tetraacyldisaccharide 4'-kinase which catalyzes the reaction: ATP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6-)-2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl beta-phosphate = ADP + 2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R,3R,4R,5S,6R)-5-hydroxy-2-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylaminooxan-4-yl (3R)-3-hydroxytetradecanoate
  • (2R,3R,4R,5S,6R)-5-Hydroxy-2-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylaminooxan-4-yl (3R)-3-hydroxytetradecanoic acid
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphoric acid
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphoric acid
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-b-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-b-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-beta-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-beta-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-β-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxytetradecanoyl-β-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphoric acid
  • 2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphate
  • 2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphoric acid
  • 2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphate
  • 2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphoric acid
  • 2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphate
  • 2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphoric acid
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-b-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ONO-a-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-beta-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ono-alpha-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-β-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ONO-α-D-glucopyranose
  • 2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphate
  • 2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphoric acid
  • 2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphate
  • 2-N,3-O-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphoric acid
  • 2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate
  • 2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphoric acid
  • Lipid A disaccharide
  • Lipid A-disaccharide-1-P
  • Lipid A-disaccharide-1-phosphate
  • Lipid a-disaccharide-1-phosphoric acid
  • Tetraacyldisaccharide 1-phosphate
  • Tetraacyldisaccharide 1-phosphoric acid
Chemical Formula:C68H129N2O20P
Weight:Average: 1325.727
Monoisotopic: 1324.88763109
InChI Key:HLDJGHAAKRKPAV-QDORLFPLSA-N
InChI:InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:lipid A-disaccharide-1-P
SMILES:CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Saccharolipid
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Hydroxy acid
  • N-acyl-amine
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.85ALOGPS
logP12.92ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.17ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area346.86 ŲChemAxon
Rotatable Bond Count60ChemAxon
Refractivity346.73 m³·mol⁻¹ChemAxon
Polarizability156.15 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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
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, Positivesplash10-0a5i-9077000000-fb97c94534c7d2e30470View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9132001010-45398bc37124f083ab02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-9542100060-e4b149d832201050e4b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9213012000-f08e8ce45347e7162adcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100001000-c18a6ea9cb3a8e40c69cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-72748762d9de8d450bf3View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18380
HMDB IDNot Available
Pubchem Compound ID13831140
Kegg IDC04932
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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.