2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate (ECMDB20056) (M2MDB000905)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (457)
Record Information
Version2.0
Creation Date2012-05-31 14:25:09 -0600
Update Date2015-06-03 17:19:13 -0600
Secondary Accession Numbers
  • ECMDB20056
Identification
Name:2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
Description2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2'-3'-diacyl-GlcN(β-1'-6)2,3-diacyl-GlcN-1-P
  • 2'-3'-Diacyl-GLCN(b-1'-6)2,3-diacyl-GLCN-1-P
  • 2'-3'-Diacyl-GlcN(beta-1'-6)2,3-diacyl-GlcN-1-P
  • 2'-3'-Diacyl-GLCN(β-1'-6)2,3-diacyl-GLCN-1-P
  • 2,3,2',3'-tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphoric acid
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-a-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-a-D-glucosamine 1-phosphoric acid
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-alpha-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-alpha-D-glucosamine 1-phosphoric acid
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphate
  • 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphoric 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-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-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-a-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-a-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-alpha-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-alpha-phosphoric acid
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphate
  • 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphoric acid
  • Lipid a disaccharide
  • Lipid A dSc
  • Tetraacyldisaccharide-1-phosphate
  • Tetraacyldisaccharide-1-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 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]
  • [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]
Chemical Formula:C68H129N2O20P
Weight:Average: 1325.727
Monoisotopic: 1324.88763109
InChI Key:HLDJGHAAKRKPAV-XFXUPMIZSA-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:(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]tetradecanecarboximidate
Traditional IUPAC Name:(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]tetradecanecarboximidate
SMILES:[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OP(O)(O)=O)[C@]([H])(N=C(O)CC([H])(O)CCCCCCCCCCC)[C@@]([H])(OC(=O)CC([H])(O)CCCCCCCCCCC)[C@]2([H])O)[C@]1([H])N=C(O)CC([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
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Carbonyl group
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic nitrogen compound
  • Organic anion
  • 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 Solubility0.0033 g/LALOGPS
logP5.9ALOGPS
logP14.56ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area359.5 ŲChemAxon
Rotatable Bond Count60ChemAxon
Refractivity368.87 m³·mol⁻¹ChemAxon
Polarizability154.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
Adenosine triphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate > ADP + Hydrogen ion + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate <> Uridine 5'-diphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
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-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine > Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Adenosine triphosphate <> Hydrogen ion + lipid IV<sub>A</sub> + ADP
Adenosine triphosphate + 2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate <> ADP +2 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
Adenosine triphosphate + 2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate <> ADP +2 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:
  • 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 ID18380
HMDB IDNot Available
Pubchem Compound ID440543
Kegg IDC04932
ChemSpider ID389445
Wikipedia IDNot Available
BioCyc IDBISOHMYR-GLC
EcoCyc IDBISOHMYR-GLC

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.
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).