P. aeruginosa Metabolome Database: (KDO)2-lipid A (PAMDB006296)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB006296

Identification

Name:

(KDO)2-lipid A

Description:

(KDO)2-lipid A is an intermediate in the synthesis of LPS. It has two 3-deoxy-D-manno-octulosonic acid (KDO) sugar residues in place of the core, and has no O-antigen.

Structure

Synonyms:

Not Available

Chemical Formula:

C₁₁₀H₁₉₆N₂O₃₉P₂

Average Molecular Weight:

2232.704

Monoisotopic Molecular Weight:

2231.292339975

InChI Key:

DIXUKJUHGLIZGU-OIPVZEHTSA-H

InChI:

InChI=1S/C110H202N2O39P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138)/p-6/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

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])(O[C@@]4(C[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O4)[C@]([H])(O)CO)C([O-])=O)[C@@]([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

Taxonomy Description

Not Available

Kingdom

Not Available

Super Class

Not Available

Class

Not Available

Sub Class

Not Available

Direct Parent

Not Available

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Not Available

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Lauroyl-KDO2-lipid IV(A) + myristoyl-[acp] > a holo-[acyl-carrier protein] + (KDO)2-lipid A
(KDO)2-lipid A + ADP-L-glycero-beta-D-manno-heptose > Hydrogen ion + Adenosine diphosphate + heptosyl-Kdo2-lipid A + ADP + Heptosyl-KDO2-lipid A
2 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + (KDO)2-lipid A >2 di-trans,octa-cis-undecaprenyl diphosphate + L-Ara4N-modified KDO2-Lipid A

SMPDB Pathways:

Lipopolysaccharide biosynthesis	PW000831
lipopolysaccharide biosynthesis II	PW001905
lipopolysaccharide biosynthesis III	PW002059
polymyxin resistance	PW002052

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Lipopolysaccharide biosynthesis pae00540

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000x-1290000000-11ae518f9b6e3d1febec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-2290000000-1fe35c45b114339ac9d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8961100000-83ffd298ca91aa9bb219	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-3190000000-ca0d72bf7d698f820ffa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0umi-9742000000-c7f89f307f213742d992	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06vi-9320000000-fe409eb62d6fb5c8e661	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link

Enzymes

Protein Details

• Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase

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
Locus Tag:: PA3556
Molecular weight:: 61.7 kDa

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.

Protein Details

• Lipopolysaccharide heptosyltransferase 1

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: Heptose transfer to the lipopolysaccharide core. It transfers the innnermost heptose to [4'-P](3-deoxy-D-manno- octulosonic acid)2-IVA
Gene Name:: rfaC
Locus Tag:: PA5011
Molecular weight:: 39.7 kDa