(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) (PAMDB003481)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003481
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
🔍MOLSDFPDBSMILESInChIView Structure
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-hydroxytetradecanoylamino}-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-hydroxytetradecanoylamino}-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-hydroxytetradecanoylamino}-1-O-phosphonato-α-D-glucopyranose
Chemical Formula: C68H126N2O23P2
Average Molecular Weight: 1401.6752
Monoisotopic Molecular Weight: 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
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
  • Disaccharide phosphate
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Monoalkyl phosphate
  • Amino saccharide
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0204 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count62ChemAxon
Refractivity377.5 m3·mol-1ChemAxon
Polarizability158.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
(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??)-lipid IVA + Cytidine monophosphate
Pathways:
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 ID8504584
Wikipedia IDNot Available
BioCyc IDNot Available