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Kdo-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA (M2MDB001742)

Record Information
Version2.0
Creation Date2012-07-30 14:55:22 -0600
Update Date2015-06-03 17:21:12 -0600
Secondary Accession Numbers
  • ECMDB21343
Identification
Name:Kdo-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
DescriptionKDO-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA is an intermediate involved in LPS (lipopolysaccharide) biosynthesis. It is a substrate for the enzyme Lipopolysaccharide core biosynthesis protein (rfaZ). It is also a substrate for Lipopolysaccharide core biosynthesis protein (rfaS).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Kdo-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
Chemical Formula:C139H241N2O70P4
Weight:Average: 3184.2673
Monoisotopic: 3182.43105031
InChI Key:HKWVBDGTKAFRJF-UHFFFAOYSA-C
InChI:InChI=1S/C139H252N2O70P4/c1-7-13-19-25-31-37-38-44-50-56-62-68-102(159)193-87(66-60-54-48-42-35-29-23-17-11-5)72-104(161)197-125-106(141-100(157)71-86(65-59-53-47-41-34-28-22-16-10-4)192-101(158)67-61-55-49-43-36-30-24-18-12-6)129(190-82-97-109(164)124(196-103(160)70-85(148)64-58-52-46-40-33-27-21-15-9-3)105(130(194-97)211-215(186,187)188)140-99(156)69-84(147)63-57-51-45-39-32-26-20-14-8-2)195-98(123(125)208-212(177,178)179)83-191-137(134(171)172)75-96(204-139(136(175)176)74-95(108(163)118(206-139)91(152)78-144)203-138(135(173)174)73-88(149)107(162)117(205-138)90(151)77-143)122(121(207-137)93(154)80-146)201-133-115(170)126(128(210-214(183,184)185)119(199-133)92(153)79-145)202-132-114(169)112(167)127(209-213(180,181)182)120(200-132)94(155)81-189-131-113(168)110(165)111(166)116(198-131)89(150)76-142/h84-98,105-133,142-155,162-170H,7-83H2,1-6H3,(H,140,156)(H,141,157)(H,171,172)(H,173,174)(H,175,176)(H2,177,178,179)(H2,180,181,182)(H2,183,184,185)(H2,186,187,188)/p-11
CAS number:Not Available
IUPAC Name:4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-2-[(5-{[3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-({3-hydroxy-5-[(3-hydroxy-1-oxidotetradecylidene)amino]-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl}methoxy)-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl)methoxy]oxane-2-carboxylate
Traditional IUPAC Name:4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-3,4-dihydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-2-[(5-{[3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-({3-hydroxy-5-[(3-hydroxy-1-oxidotetradecylidene)amino]-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl}methoxy)-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl)methoxy]oxane-2-carboxylate
SMILES:CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP([O-])([O-])=O)C(COC2(CC(OC3(CC(OC4(CC(O)C(O)C(O4)C(O)CO)C([O-])=O)C(O)C(O3)C(O)CO)C([O-])=O)C(OC3OC(C(O)CO)C(OP([O-])([O-])=O)C(OC4OC(C(O)COC5OC(C(O)CO)C(O)C(O)C5O)C(OP([O-])([O-])=O)C(O)C4O)C3O)C(O2)C(O)CO)C([O-])=O)OC(OCC2OC(OP(O)(O)=O)C(N=C([O-])CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)C1N=C([O-])CC(CCCCCCCCCCC)OC(=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:-10
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.02 g/LALOGPS
logP2.6ALOGPS
logP13.71ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)0.19ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count64ChemAxon
Hydrogen Donor Count25ChemAxon
Polar Surface Area1184.19 ŲChemAxon
Rotatable Bond Count119ChemAxon
Refractivity791.6 m³·mol⁻¹ChemAxon
Polarizability333.09 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
CMP-3-Deoxy-D-manno-octulosonate + Phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA > Cytidine monophosphate + Hydrogen ion + Kdo-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
Deoxythymidine diphosphate-L-rhamnose + Kdo-phospho-heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA > dTDP + Hydrogen ion + inner core oligosaccharide lipid A (E coli)
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 ID46173523
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2257
EcoCyc IDCPD0-2257

Enzymes

Protein Details
1. Lipopolysaccharide core biosynthesis protein rfaZ
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Specific function unknown
Gene Name:
rfaZ
Uniprot ID:
P27241
Molecular weight:
32920
Protein Details
2. Lipopolysaccharide core biosynthesis protein rfaS
General function:
Involved in protein binding
Specific function:
Specific function unknown
Gene Name:
rfaS
Uniprot ID:
P27126
Molecular weight:
36730