2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (PAMDB003483)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003483
Identification
Name: 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Description:2,3-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
🔍MOLSDFPDBSMILESInChIView Structure
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-phosphONO-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-phosphono-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-phosphONO-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
Average Molecular Weight: 1325.727
Monoisotopic Molecular Weight: 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
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
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • 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:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00172 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count60ChemAxon
Refractivity346.73 m3·mol-1ChemAxon
Polarizability156.15 Å3ChemAxon
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
Pathways: 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 ID21864852
Wikipedia IDNot Available
BioCyc IDNot Available