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Phospho-heptosyl-heptosyl-kdo2-lipidA (M2MDB001748)

Record Information
Version2.0
Creation Date2012-07-30 14:55:24 -0600
Update Date2015-06-03 17:21:12 -0600
Secondary Accession Numbers
  • ECMDB21350
Identification
Name:Phospho-heptosyl-heptosyl-kdo2-lipidA
DescriptionPhospho-heptosyl-heptosyl-kdo2-lipida belongs to the class of Hexose Oligosaccharides. These are oligosaccharides in which the saccharide units are hexoses. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Phospho-heptosyl-heptosyl-kdo2-lipidA
Chemical Formula:C124H219N2O54P3
Weight:Average: 2694.9679
Monoisotopic: 2693.366504142
InChI Key:XNYUHCDJIRFEJF-LIOVHSHWSA-F
InChI:InChI=1S/C124H227N2O54P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(141)166-84(66-60-54-48-42-35-29-23-17-11-5)72-98(143)170-114-100(126-94(139)71-83(65-59-53-47-41-34-28-22-16-10-4)165-95(140)67-61-55-49-43-36-30-24-18-12-6)117(163-79-91-102(145)113(169-97(142)70-82(132)64-58-52-46-40-33-27-21-15-9-3)99(118(167-91)180-183(160,161)162)125-93(138)69-81(131)63-57-51-45-39-32-26-20-14-8-2)168-92(112(114)178-181(154,155)156)80-164-123(121(150)151)74-90(175-124(122(152)153)73-85(133)101(144)108(176-124)87(135)76-128)111(110(177-123)89(137)78-130)173-120-106(149)115(105(148)107(171-120)86(134)75-127)174-119-104(147)103(146)116(179-182(157,158)159)109(172-119)88(136)77-129/h81-92,99-120,127-137,144-149H,7-80H2,1-6H3,(H,125,138)(H,126,139)(H,150,151)(H,152,153)(H2,154,155,156)(H2,157,158,159)(H2,160,161,162)/p-8/t81-,82-,83-,84-,85?,86+,87?,88+,89-,90-,91-,92-,99-,100-,101?,102-,103-,104+,105-,106+,107?,108?,109?,110-,111-,112-,113-,114-,115+,116+,117-,118-,119?,120?,123-,124?/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}-6-[(1R)-1,2-dihydroxyethyl]-5-{[(3S,4S,5R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4R,5S)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-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}-6-[(1R)-1,2-dihydroxyethyl]-5-{[(3S,4S,5R)-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4R,5S)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-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)CO)[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
  • 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 Solubility0.19 g/LALOGPS
logP3.58ALOGPS
logP17.72ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)0.38ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count49ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area913.34 ŲChemAxon
Rotatable Bond Count108ChemAxon
Refractivity690.55 m³·mol⁻¹ChemAxon
Polarizability288.41 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Adenosine triphosphate + heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + 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 ID46173154
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2240
EcoCyc IDCPD0-2240

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