Record Information
Version2.0
Creation Date2012-07-30 14:55:04 -0600
Update Date2015-06-03 17:20:58 -0600
Secondary Accession Numbers
  • ECMDB21235
Identification
Name:KDO(2)-lipid IV(A)
DescriptionKdo(2)-lipid iv(a) belongs to the class of Polysaccharide Phosphates. These are polysaccharides in which a phosphate group is bound to at least one carbohydrate unit. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • (2R,4R,5R,6R)-2-(2R,4R,5R,6R)-2-Carboxy-6-(1R)-1,2-dihydroxyethyl-5-hydroxy-2-(2R,3S,4R,5R,6R)-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-3-phosphonooxyoxan-2-ylmethoxyoxan-4-yloxy-6-(1R)-1,2-dihydroxyethyl-4,5-dihydroxyoxane-2-carboxylate
  • (2R,4R,5R,6R)-2-(2R,4R,5R,6R)-2-carboxy-6-(1R)-1,2-dihydroxyethyl-5-hydroxy-2-(2R,3S,4R,5R,6R)-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-3-phosphonooxyoxan-2-ylmethoxyoxan-4-yloxy-6-(1R)-1,2-dihydroxyethyl-4,5-dihydroxyoxane-2-carboxylic acid
  • (2R,4R,5R,6R)-4-(2R,4R,5R,6R)-2-Carboxy-6-(1R)-1,2-dihydroxyethyl-4,5-dihydroxy-tetrahydropyran-2-yloxy-6-(1R)-1,2-dihydroxyethyl-5-hydroxy-2-(2R,3S,4R,5R,6R)-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxy-tetrahydropyran-2-ylmethoxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-3-phosphonooxy-tetrahydropyran-2-ylmethoxytetrahydropyran-2-carboxylate
  • (2R,4R,5R,6R)-4-(2R,4R,5R,6R)-2-carboxy-6-(1R)-1,2-dihydroxyethyl-4,5-dihydroxy-tetrahydropyran-2-yloxy-6-(1R)-1,2-dihydroxyethyl-5-hydroxy-2-(2R,3S,4R,5R,6R)-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxy-tetrahydropyran-2-ylmethoxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-3-phosphonooxy-tetrahydropyran-2-ylmethoxytetrahydropyran-2-carboxylic acid
  • Di3-deoxy-D-manno-octulosonyl-lipid IV(A)
  • KDO2-lipid IV(A)
Chemical Formula:C84H154N2O37P2
Weight:Average: 1846.0603
Monoisotopic: 1844.970566976
InChI Key:XAOLJGCZESYRFT-VHSKNIDJSA-N
InChI:InChI=1S/C84H154N2O37P2/c1-5-9-13-17-21-25-29-33-37-41-55(89)45-65(96)85-69-77(117-67(98)47-57(91)43-39-35-31-27-23-19-15-11-7-3)73(102)63(115-80(69)123-125(110,111)112)53-113-79-70(86-66(97)46-56(90)42-38-34-30-26-22-18-14-10-6-2)78(118-68(99)48-58(92)44-40-36-32-28-24-20-16-12-8-4)76(122-124(107,108)109)64(116-79)54-114-83(81(103)104)50-62(72(101)75(120-83)61(95)52-88)119-84(82(105)106)49-59(93)71(100)74(121-84)60(94)51-87/h55-64,69-80,87-95,100-102H,5-54H2,1-4H3,(H,85,96)(H,86,97)(H,103,104)(H,105,106)(H2,107,108,109)(H2,110,111,112)/t55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,83-,84-/m1/s1
CAS number:143600-83-3
IUPAC Name:(2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-hydroxy-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}oxane-2-carboxylic acid
Traditional IUPAC Name:(kdo)2-lipid iva
SMILES:[H]OC(=O)[C@]1(OC([H])([H])[C@@]2([H])O[C@@]([H])(OC([H])([H])[C@@]3([H])O[C@]([H])(OP(=O)(O[H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]3([H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]2([H])OP(=O)(O[H])O[H])O[C@]([H])([C@]([H])(O[H])C([H])([H])O[H])[C@]([H])(O[H])[C@]([H])(O[C@]2(O[C@]([H])([C@]([H])(O[H])C([H])([H])O[H])[C@]([H])(O[H])[C@]([H])(O[H])C2([H])[H])C(=O)O[H])C1([H])[H]
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
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Tetracarboxylic acid or derivatives
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Ketal
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • N-acyl-amine
  • Alkyl phosphate
  • Pyran
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Organopnictogen compound
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-6
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP9.83ChemAxon
pKa (Strongest Acidic)0.6ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count33ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area626.29 ŲChemAxon
Rotatable Bond Count72ChemAxon
Refractivity444.02 m³·mol⁻¹ChemAxon
Polarizability195.55 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
  • superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28526
HMDB IDNot Available
Pubchem Compound ID3083382
Kegg IDC06025
ChemSpider ID2340609
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Essential step in lipopolysaccharides biosynthesis. Acts at transfer of 3-deoxy-D-mono octulonic acid (KDO) from CMP-KDO to a tetraacyldisaccharide 1,4'-bisphosphate precursor of lipid A (lipid IVA). Transfers two molecules of KDO to lipid IVA. Degraded by FtsH; therefore FtsH regulates the addition of the sugar moiety of the LPS and thus the maturation of the LPS precursor
Gene Name:
waaA
Uniprot ID:
P0AC75
Molecular weight:
47291
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Acylates the intermediate (KDO)2-lipid IVA to form (KDO)2-(lauroyl)-lipid IVA. Has 10 fold selectivity for lauroyl- ACP over myristoyl-ACP
Gene Name:
htrB
Uniprot ID:
P0ACV0
Molecular weight:
35407
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnT
Uniprot ID:
P76473
Molecular weight:
62542
Reactions
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + lipid IV(A) = lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate.
General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Uniprot ID:
P0ADC6
Molecular weight:
39618
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Uniprot ID:
P0AF98
Molecular weight:
40357
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Specific function unknown
Gene Name:
ddg
Uniprot ID:
P0ACV2
Molecular weight:
35493
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. Probably responsible for energy coupling to the transport system
Gene Name:
lptB
Uniprot ID:
P0A9V1
Molecular weight:
26800
General function:
Involved in lipopolysaccharide transmembrane transporter activity
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptC
Uniprot ID:
P0ADV9
Molecular weight:
21703
General function:
Involved in lipopolysaccharide binding
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. May act as a chaperone that facilitates LPS transfer across the aquaeous environment of the periplasm. Interacts specifically with the lipid A domain of LPS
Gene Name:
lptA
Uniprot ID:
P0ADV1
Molecular weight:
20127

Transporters

General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Uniprot ID:
P0ADC6
Molecular weight:
39618
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Uniprot ID:
P0AF98
Molecular weight:
40357
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460