P. aeruginosa Metabolome Database: α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A (PAMDB110365)

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

PAMDB110365

Identification

Name:

α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A

Description:

A carbohydrate acid derivative anion that is the hexa-anion of Kdo₂-lipid A arising from deprotonation of both the carboxyl and phosphate functions.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Re endotoxin
(Kdo)₂-lipid A
Kdo₂-lipid A

Chemical Formula:

C₁₁₀H₁₉₆N₂O₃₉P₂

Average Molecular Weight:

2232.7

Monoisotopic Molecular Weight:

2237.3359977765

InChI Key:

DIXUKJUHGLIZGU-PPLOIMQXSA-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:

3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→4)-3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→6)-2-deoxy-2-[(3R)-3-(dodecanoyloxy)tetradecanamido]-4-O-phosphonato-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl-(1→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphonato-α-D-glucopyranose

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC4(C(C(OCC1(OC(OP([O-])([O-])=O)C(NC(CC(O)CCCCCCCCCCC)=O)C(OC(CC(O)CCCCCCCCCCC)=O)C(O)1))OC(COC3(C([O-])=O)(O[CH](C(CO)O)C(O)C(OC2(C([O-])=O)(O[CH](C(CO)O)C(O)C(O)C2))C3))C4OP([O-])([O-])=O)NC(CC(OC(CCCCCCCCCCC)=O)CCCCCCCCCCC)=O)

Chemical Taxonomy

Taxonomy Description

This compound 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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Oligosaccharide phosphate
Oligosaccharide
Hexacarboxylic acid or derivatives
Acylaminosugar
Saccharolipid
Hexose phosphate
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Ketal
Fatty acid ester
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
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Acetal
Primary alcohol
Organopnictogen compound
Alcohol
Organic oxide
Carbonyl group
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a 3-deoxyoctulosonyl-lipopolysaccharide (KDO2-LIPID-A)

Physical Properties

State:

Not Available

Charge:

-6

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	2232.701 g/mol	PubChem
XLogP3-AA	23.6	PubChem
Hydrogen Bond Donor Count	12	PubChem
Hydrogen Bond Acceptor Count	39	PubChem
Rotatable Bond Count	94	PubChem
Exact Mass	2232.292 g/mol	PubChem
Monoisotopic Mass	2231.289 g/mol	PubChem
Topological Polar Surface Area	655 A^2	PubChem
Heavy Atom Count	153	PubChem
Formal Charge	-6	PubChem
Complexity	3730	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	24	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 + ADP-L-glycero-beta-D-manno-heptose → heptosyl-Kdo2-lipid A + ADP + Hydrogen ion
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:

KDO₂-lipid A and peptidoglycan biosynthesisKDO-PEP-LIPASYN-PWY
superpathway of (Kdo)₂-lipid A biosynthesisKDO-NAGLIPASYN-PWY
(KDO)₂-lipid A biosynthesis IKDO-LIPASYN-PWY
polymyxin resistancePWY0-1338
Lipid A-core biosynthesisLIPA-CORESYN-PWY
superpathway of lipopolysaccharide biosynthesisLPSSYN-PWY

Spectra

Spectra:

Not Available

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
ChEBI	58540
IAF1260	47241
KEGG	C06026
PubChem	25244473

α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A (PAMDB110365)

Structure for α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A (PAMDB110365)