P. aeruginosa Metabolome Database: 4'-α-L-Ara4<i>N</i>-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-α-L-ara4<i>N</i>]-lipid A (PAMDB120074)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB120074

Identification

Name:

4'-α-L-Ara4N-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-α-L-ara4N]-lipid A

Description:

A lipid A oxoanion obtained by deprotonation of the phosphate and carboxy groups and protonation of the free amino groups of (β-L-Ara4N)₂-(KDO)₂-lipid A; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(β-L-Ara4N)₂-(Kdo)₂-lipid A
4'-β-L-Ara4N-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-β-L-ara4N]-lipid A(2−)
L-Ara4N-modified (KDO)2-Lipid A

Chemical Formula:

C₁₂₀H₂₁₈N₄O₄₅P₂

Average Molecular Weight:

2498.989

Monoisotopic Molecular Weight:

2501.468

InChI Key:

RYVJLJVPSMBXLB-SWFLZAEGSA-L

InChI:

InChI=1S/C120H220N4O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(135)158-84(66-60-54-48-42-35-29-23-17-11-5)72-98(137)162-112-100(124-94(133)71-83(65-59-53-47-41-34-28-22-16-10-4)157-95(134)67-61-55-49-43-36-30-24-18-12-6)113(160-92(110(112)166-170(149,150)168-115-106(143)101(138)85(121)77-153-115)80-156-119(117(145)146)74-90(104(141)109(164-119)89(131)76-126)163-120(118(147)148)73-87(129)103(140)108(165-120)88(130)75-125)155-79-91-105(142)111(161-97(136)70-82(128)64-58-52-46-40-33-27-21-15-9-3)99(123-93(132)69-81(127)63-57-51-45-39-32-26-20-14-8-2)114(159-91)167-171(151,152)169-116-107(144)102(139)86(122)78-154-116/h81-92,99-116,125-131,138-144H,7-80,121-122H2,1-6H3,(H,123,132)(H,124,133)(H,145,146)(H,147,148)(H,149,150)(H,151,152)/p-2/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-,119-,120-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCCCCCCCC(OC(CCCCCCCCCCC)CC(=O)OC6(C(OP(=O)([O-])OC1(C(C(C(CO1)[N+])O)O))C(COC2(CC(C(C(O2)C(CO)O)O)OC3(CC(C(C(O3)C(CO)O)O)O)C(=O)[O-])C(=O)[O-])OC(OCC5(C(C(C(C(OP([O-])(=O)OC4(C(C(C(CO4)[N+])O)O))O5)NC(CC(CCCCCCCCCCC)O)=O)OC(CC(CCCCCCCCCCC)O)=O)O))C(NC(=O)CC(OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)6))=O

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:

-2

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	2498.995 g/mol	PubChem
XLogP3-AA	15.7	PubChem
Hydrogen Bond Donor Count	18	PubChem
Hydrogen Bond Acceptor Count	45	PubChem
Rotatable Bond Count	100	PubChem
Exact Mass	2498.44 g/mol	PubChem
Monoisotopic Mass	2497.437 g/mol	PubChem
Topological Polar Surface Area	782 A^2	PubChem
Heavy Atom Count	171	PubChem
Formal Charge	-2	PubChem
Complexity	4340	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	32	PubChem
Undefined Atom Stereocenter Count	0	PubChem
Defined Bond Stereocenter Count	0	PubChem
Undefined Bond Stereocenter Count	0	PubChem
Covalently-Bonded Unit Count	1	PubChem

Biological Properties

Cellular Locations:

Not Available

Reactions:

α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose → 4'-α-L-Ara4N-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-α-L-ara4N]-lipid A + di-trans,octa-cis-undecaprenyl phosphate

Pathways:

polymyxin resistancePWY0-1338

Spectra

Spectra:

Not Available

References

References:

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI	71399
PUBCHEM	25202130

4'-α-L-Ara4N-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-α-L-ara4N]-lipid A (PAMDB120074)

Structure for 4'-α-L-Ara4N-α-Kdo-(2→4)-α-Kdo-(2→6)-[P4'-α-L-ara4N]-lipid A (PAMDB120074)