Structure database (LMSD)

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LM IDLMSL02000001
Common NameKdo2-lipid A
Systematic NameKdo2-lipid A
Synonyms-
Exact Mass
2237.3360 (neutral)    Calculate m/z:
FormulaC110H202N2O39P2
CategorySaccharolipids [SL]
Main ClassAcylaminosugar glycans [SL02]
Sub Class-
PubChem CID5771770
CHEBI ID27963
InChIKeyDIXUKJUHGLIZGU-RBBLMZRZSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=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(65-59-53-47-4
1-34-28-22-16-10-4)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)76-1
14)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(1
28)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/h79-88,95-106,1
13-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133
,134,135)(H2,136,137,138)/t79-,80-,81-,82-,83?,84-,85-,86-,87?,88?,95+,96+,97-,9
8-,99-,100?,101?,102-,103?,104?,105-,106-,109-,110-/m1/s1
SMILES-
MS Spectra-     
MS StandardView lipid standard
StatusActive
References1. Raetz, C. R., Garrett, T. A., Reynolds, C. M., Shaw, W. A., Moore, J. D.,
Smith, D. C., Jr., Ribeiro, A. A., Murphy, R. C., Ulevitch, R. J., Fearns, C.,
Reichart, D., Glass, C. K., Benner, C., Subramaniam, S., Harkewicz, R.,
Bowers-Gentry, R. C., Buczynski, M. W., Cooper, J. A., Deems, R. A., and Dennis, E. A.
Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4.
J Lipid Res, 2006, 47, 1097-1111.

2. Murphy, R. C., Raetz, C. R., Reynolds, C. M., Barkley, R. M.
Mass spectrometry advances in lipidomica: collision-induced decomposition of Kdo2-lipid A.
Prostaglandins Other Lipid Mediat. 2005, 77(1-4), 131-40. Review.

3. Raetz, C. R., Reynolds, C. M., Trent, M. S., Bishop, R. E.
Lipid A modification systems in gram-negative bacteria.
Annu Rev Biochem. 2007, 76, 295-329. Review.

Calculated physicochemical properties (?):
 Heavy Atoms153Rings4Aromatic Rings0Rotatable Bonds98
 van der Waals
Molecular Volume
2245.47Topological Polar
Surface Area
646.71Hydrogen
Bond Donors
18Hydrogen
Bond Acceptors
39
 logP24.63Molar
Refractivity
581.93