Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate (M2MDB006338)

Record Information
Version2.0
Creation Date2015-09-08 17:50:09 -0600
Update Date2015-09-14 16:46:37 -0600
Secondary Accession Numbers
  • ECMDB24221
Identification
Name:glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate
DescriptionGlucosyl-(heptosyl)2-Kdo2-lipid A-phosphate is an intermediate in Lipid A-core biosynthesis pathway in E.coli. It is a substrate for the enzyme lipopolysaccharide core heptosyl transferase III which catalyzes the reaction glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP-L-glycero-beta-D-manno-heptose -> glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ADP + H+. It is also a product for enzyme lipopolysaccharide core heptose (I) kinase which catalyzes reaction glucosyl-(heptosyl)2-Kdo2-lipid A + ATP → glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP + H+ (BioCyc compound: CPD0-933).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Glucosyl-(heptosyl)2-kdo2-lipid a-phosphoric acid
Chemical Formula:C130H229N2O59P3
Weight:Average: 2857.143
Monoisotopic: 2855.423717595
InChI Key:GBPUUSBSBGYHGL-DOCZPCJQSA-F
InChI:InChI=1S/C130H237N2O59P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-98(148)175-85(66-60-54-48-42-35-29-23-17-11-5)72-100(150)180-118-102(132-96(146)71-84(65-59-53-47-41-34-28-22-16-10-4)174-97(147)67-61-55-49-43-36-30-24-18-12-6)122(172-80-93-105(153)117(179-99(149)70-83(139)64-58-52-46-40-33-27-21-15-9-3)101(123(177-93)191-194(169,170)171)131-95(145)69-82(138)63-57-51-45-39-32-26-20-14-8-2)178-94(116(118)189-192(163,164)165)81-173-129(127(159)160)74-91(186-130(128(161)162)73-86(140)103(151)112(187-130)88(142)76-134)115(114(188-129)90(144)78-136)183-126-110(158)120(121(190-193(166,167)168)113(182-126)89(143)77-135)185-125-109(157)119(108(156)111(181-125)87(141)75-133)184-124-107(155)106(154)104(152)92(79-137)176-124/h82-94,101-126,133-144,151-158H,7-81H2,1-6H3,(H,131,145)(H,132,146)(H,159,160)(H,161,162)(H2,163,164,165)(H2,166,167,168)(H2,169,170,171)/p-8/t82-,83-,84-,85-,86-,87+,88-,89+,90-,91-,92-,93-,94-,101-,102-,103-,104-,105-,106+,107-,108-,109+,110+,111-,112-,113-,114-,115-,116-,117-,118-,119+,120-,121-,122-,123-,124?,125-,126-,129-,130-/m1/s1
CAS number:Not Available
IUPAC Name:(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-5-{[(2S,3S,4R,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
Traditional IUPAC Name:(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-5-{[(2S,3S,4R,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(2R,3S,4S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
SMILES:[H][C@@]1(O[C@@](C[C@@H](O)[C@H]1O)(O[C@@H]1C[C@@](OC[C@H]2O[C@@H](OC[C@H]3O[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]3O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H]2OP([O-])([O-])=O)(O[C@]([H])([C@H](O)CO)[C@@H]1O[C@H]1O[C@H]([C@@H](O)CO)[C@@H](OP([O-])([O-])=O)[C@H](O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)[C@@H]1O)C([O-])=O)C([O-])=O)[C@H](O)CO
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
  • Oligosaccharide phosphate
  • Oligosaccharide
  • Hexacarboxylic acid or derivatives
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • C-glycosyl compound
  • Glycosyl compound
  • Fatty acid ester
  • Ketal
  • Beta-hydroxy acid
  • Pyran
  • Fatty acyl
  • Phosphoric acid ester
  • Oxane
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Fatty amide
  • Alkyl phosphate
  • Carboxamide group
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Polyol
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-8
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP2.98ALOGPS
logP14.31ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)0.31ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count52ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area985.51 ŲChemAxon
Rotatable Bond Count111ChemAxon
Refractivity698.58 m³·mol⁻¹ChemAxon
Polarizability301.07 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
glucosyl-(heptosyl)2-Kdo2-lipid A + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP
glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP-L-glycero-beta-D-manno-heptose > Adenosine diphosphate + Hydrogen ion + glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ADP
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:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID51351791
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lipopolysaccharide core heptosyltransferase rfaQ
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Catalyzes heptose transfer to the lipopolysaccharide core. It transfers a heptose, called heptose(III), to the heptose(II) of the inner core
Gene Name:
rfaQ
Uniprot ID:
P25742
Molecular weight:
38730
Protein Details
2. Lipopolysaccharide core heptose(I) kinase rfaP
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Catalyzes the phosphorylation of heptose(I) of the outer membrane lipopolysaccharide core
Gene Name:
rfaP
Uniprot ID:
P25741
Molecular weight:
30872