2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate (PAMDB000906)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000906
Identification
Name: 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
Description:2,3,2'3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. Pseudomonas aeruginosa KdtA (EcKdtA) is a bifunctional enzyme that transfers two KDO units from two CMP-KDO molecules to lipid IV(A). (PMID 20394418)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid
  • Lipid a disaccharide bisphosphate
  • Lipid a disaccharide bisphosphoric acid
  • Lipid IV(a)
Chemical Formula: C68H130N2O23P2
Average Molecular Weight: 1405.7069
Monoisotopic Molecular Weight: 1404.8539615
InChI Key: KVJWZTLXIROHIL-XFXUPMIZSA-N
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)/t51?,52?,53?,54?,55-,56-,61-,62-,63-,64-,65-,66-,67-,68+/m1/s1
CAS number: Not Available
IUPAC Name:N-[(2S,3R,4R,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3-[(1,3-dihydroxytetradecylidene)amino]-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-5-(phosphonooxy)oxan-2-yl]oxy}methyl)-5-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]-3-hydroxytetradecanimidic acid
Traditional IUPAC Name: N-[(2S,3R,4R,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3-[(1,3-dihydroxytetradecylidene)amino]-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-5-(phosphonooxy)oxan-2-yl]oxy}methyl)-5-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]-3-hydroxytetradecanimidic acid
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)CC([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C(O)CC([H])(O)CCCCCCCCCCC)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
  • 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
  • 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:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0121 mg/mLALOGPS
logP5.26ALOGPS
logP14.43ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)0.55ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area400.37 Å2ChemAxon
Rotatable Bond Count62ChemAxon
Refractivity358.65 m3·mol-1ChemAxon
Polarizability158.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Adenosine triphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate <> ADP + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate + CMP-3-Deoxy-D-manno-octulosonate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> KDO-lipid IV(A) + Cytidine monophosphate
Undecaprenyl phosphate alpha-L-Ara4N + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> Lipid IIA + Di-trans,poly-cis-undecaprenyl phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n0-0629000000-e9c2425122ab7f4df25aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g3-0945001002-37eea6ca1ab309a7bd37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qj-9854001002-2d27dbeafba1599c7c7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-8895215400-22dbdf4efd5d3a75b7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9231001100-7fd984cedff1d1cfd77cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-8ba468568bbbeed1ca7aView in MoNA
References
References:
  • Chung, H. S., Raetz, C. R. (2010). "Interchangeable domains in the Kdo transferases of Escherichia coli and Haemophilus influenzae." Biochemistry 49:4126-4137. Pubmed: 20394418
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID29056
HMDB IDNot Available
Pubchem Compound ID24892757
Kegg IDC04919
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE
EcoCyc IDDIHYDRO-DIOH-BENZOATE