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Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA (M2MDB001741)

Record Information
Version2.0
Creation Date2012-07-30 14:55:22 -0600
Update Date2015-06-03 17:21:11 -0600
Secondary Accession Numbers
  • ECMDB21342
Identification
Name:Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
DescriptionHeptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA is an intermediate involved in LPS (lipopolysaccharide) biosynthesis. It is a substrate for the enzyme Lipopolysaccharide core heptosyltransferase (rfaQ). This enzyme catalyzes heptose transfer to the lipopolysaccharide core. Specifically, it transfers a heptose, called heptose(III), to the heptose(II) of the inner core.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
Chemical Formula:C131H231N2O60P3
Weight:Average: 2887.1345
Monoisotopic: 2885.429892258
InChI Key:OCKKDDJUVZAABC-XSAOWLIJSA-F
InChI:InChI=1S/C131H239N2O60P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-98(149)178-85(66-60-54-48-42-35-29-23-17-11-5)72-100(151)182-120-102(133-96(147)71-84(65-59-53-47-41-34-28-22-16-10-4)177-97(148)67-61-55-49-43-36-30-24-18-12-6)123(175-80-93-104(153)119(181-99(150)70-83(139)64-58-52-46-40-33-27-21-15-9-3)101(124(179-93)193-196(171,172)173)132-95(146)69-82(138)63-57-51-45-39-32-26-20-14-8-2)180-94(118(120)191-194(165,166)167)81-176-130(128(161)162)74-92(188-131(129(163)164)73-86(140)103(152)114(189-131)89(143)77-136)117(116(190-130)90(144)78-137)186-127-111(160)121(110(159)113(184-127)88(142)76-135)187-126-109(158)107(156)122(192-195(168,169)170)115(185-126)91(145)79-174-125-108(157)105(154)106(155)112(183-125)87(141)75-134/h82-94,101-127,134-145,152-160H,7-81H2,1-6H3,(H,132,146)(H,133,147)(H,161,162)(H,163,164)(H2,165,166,167)(H2,168,169,170)(H2,171,172,173)/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?,127?,130-,131?/m1/s1
CAS number:Not Available
IUPAC Name:(2R,4R,5R,6R)-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-5-{[(3S,4S,5R)-4-{[(3S,4R,5S)-6-[(1S)-2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(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}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylate
Traditional IUPAC Name:(2R,4R,5R,6R)-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-5-{[(3S,4S,5R)-4-{[(3S,4R,5S)-6-[(1S)-2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-3,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(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}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylate
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@@]3(C[C@@]([H])(OC4(CC([H])(O)C([H])(O)C([H])(O4)C([H])(O)CO)C([O-])=O)[C@@]([H])(OC4([H])OC([H])([C@@]([H])(O)CO)[C@@]([H])(O)[C@]([H])(OC5([H])OC([H])([C@@]([H])(O)COC6([H])OC([H])(C([H])(O)CO)C([H])(O)C([H])(O)C6([H])O)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(O)[C@]5([H])O)[C@]4([H])O)[C@]([H])(O3)[C@]([H])(O)CO)C([O-])=O)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([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
  • Oligosaccharide phosphate
  • Oligosaccharide
  • Hexacarboxylic acid or derivatives
  • Saccharolipid
  • Acylaminosugar
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Ketal
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Hydroxy acid
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-7
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP3.09ALOGPS
logP15.31ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)0.38ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count55ChemAxon
Hydrogen Donor Count23ChemAxon
Polar Surface Area1012.72 ŲChemAxon
Rotatable Bond Count112ChemAxon
Refractivity728.93 m³·mol⁻¹ChemAxon
Polarizability307.59 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Adenosine triphosphate + Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + Phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
ADP-L-Glycero-D-manno-heptose + Phospho-heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
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 ID46173497
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2238
EcoCyc IDCPD0-2238

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(II) kinase rfaY
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Catalyzes the phosphorylation of heptose(II) of the outer membrane lipopolysaccharide core
Gene Name:
rfaY
Uniprot ID:
P27240
Molecular weight:
27461