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(2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) (M2MDB003481)

Record Information
Version2.0
Creation Date2012-10-10 12:15:45 -0600
Update Date2015-06-03 17:25:54 -0600
Secondary Accession Numbers
  • ECMDB23091
Identification
Name:(2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate)
Description(2-N,3-O-bis(3-hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) is a substrate for tetraacyldisaccharide 4'-kinase. This is an enzyme that phosphorylates the 4'-position of a tetraacyldisaccharide 1-phosphate precursor (DS-1-P) of lipopolysaccharide lipid A. This lipid which is part of LPS, forms the outer membranes of Gram-negative bacteria. This enzyme catalyzes the chemical reaction: ATP + [2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl]-(1->6)-[2- N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate] <=> ADP + [2-N,3-O-bis(3-hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D- glucosaminyl phosphate]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2-N,3-O-Bis(3-hydroxytetradecanoyl)-4-O-phosphono-b-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl phosphate)
  • (2-N,3-O-Bis(3-hydroxytetradecanoyl)-4-O-phosphono-b-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl phosphoric acid)
  • (2-N,3-O-Bis(3-hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphoric acid)
  • (2-N,3-O-Bis(3-hydroxytetradecanoyl)-4-O-phosphono-β-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl phosphate)
  • (2-N,3-O-Bis(3-hydroxytetradecanoyl)-4-O-phosphono-β-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl phosphoric acid)
  • (2R,3R,4R,5S,6R)-5-hydroxy-6-(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-5-phosphonatooxyoxan-2-yloxymethyl-3-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxyoxan-2-yl phosphate
  • (2R,3R,4R,5S,6R)-5-Hydroxy-6-(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-5-phosphonatooxyoxan-2-yloxymethyl-3-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxyoxan-2-yl phosphoric acid
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-4-O-phosphonato-b-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoyla mino}-1-O-phosphonato-a-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-4-O-phosphonato-beta-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoyla mino}-1-O-phosphonato-alpha-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-4-O-phosphonato-β-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoyla mino}-1-O-phosphonato-α-D-glucopyranose
Chemical Formula:C68H126N2O23P2
Weight:Average: 1401.6752
Monoisotopic: 1400.822661372
InChI Key:KVJWZTLXIROHIL-QDORLFPLSA-J
InChI:InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/p-4/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1
CAS number:Not Available
IUPAC Name:(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-3-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-2-yl]oxy}methyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-2-(phosphonooxy)oxan-3-yl]tetradecanecarboximidate
Traditional IUPAC Name:(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-3-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-2-yl]oxy}methyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-2-(phosphonooxy)oxan-3-yl]tetradecanecarboximidate
SMILES:[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([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
  • Hexose phosphate
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • N-acyl-amine
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP5.44ALOGPS
logP14.43ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.55ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area411.69 ŲChemAxon
Rotatable Bond Count62ChemAxon
Refractivity377.5 m³·mol⁻¹ChemAxon
Polarizability158.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Adenosine triphosphate + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) > ADP + (2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate)
(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + (2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) + ADP
CMP-3-Deoxy-D-manno-octulosonate + (2-N,3-O-bis(3-Hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) > Cytidine monophosphate + Hydrogen ion + alpha-Kdo-(2→6)-lipid IVA + Cytidine monophosphate
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1209500000-f481f37bcc73ee85f6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1119000000-a1a776f8bb4a9d19fe3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-5934000100-8dda81f0a736bf7d7368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2219000000-062b420884fe32a4eb3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-6669000000-4261b43e6a32b1dabc17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9220000000-180f26217350f91d2993View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58603
HMDB IDNot Available
Pubchem Compound ID10329123
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-deoxy-D-manno-octulosonic-acid transferase
General function:
Involved in biosynthetic process
Specific function:
Essential step in lipopolysaccharides biosynthesis. Acts at transfer of 3-deoxy-D-mono octulonic acid (KDO) from CMP-KDO to a tetraacyldisaccharide 1,4'-bisphosphate precursor of lipid A (lipid IVA). Transfers two molecules of KDO to lipid IVA. Degraded by FtsH; therefore FtsH regulates the addition of the sugar moiety of the LPS and thus the maturation of the LPS precursor
Gene Name:
waaA
Uniprot ID:
P0AC75
Molecular weight:
47291
Protein Details
2. Tetraacyldisaccharide 4'-kinase
General function:
Involved in ATP binding
Specific function:
Transfers the gamma-phosphate of ATP to the 4'-position of a tetraacyldisaccharide 1-phosphate intermediate (termed DS-1- P) to form tetraacyldisaccharide 1,4'-bis-phosphate (lipid IVA)
Gene Name:
lpxK
Uniprot ID:
P27300
Molecular weight:
35589
Reactions
ATP + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) = ADP + (2-N,3-O-bis(3-hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate).