Structure Database (LMSD)
Common Name
Kdo2-lipid A
Systematic Name
Kdo2-lipid A
Synonyms
Main
Classification
String Representations
InChiKey (Click to copy)
DIXUKJUHGLIZGU-AWSPPZEXSA-N
InChi (Click to copy)
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)/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
SMILES (Click to copy)
P(O[C@@H]1[C@@H](CO[C@]2(C(=O)O)C[C@@H](O[C@]3(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@@H](CO)O)O3)[C@@H](O)[C@@H]([C@@H](CO)O)O2)O[C@H](OC[C@@H]2[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(=O)O)O2)[C@H](NC(=O)C[C@H](OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)[C@H]1OC(=O)C[C@H](OC(=O)CCCCCCCCCCCCC)CCCCCCCCCCC)(=O)(O)O
References
Reference
1. 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.
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.
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Escherichia coli
(#562)
Gammaproteobacteria
(#1236)
Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4.,
J Lipid Res, 2006
J Lipid Res, 2006
Pubmed ID:
16479018
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
153
Rings
4
Aromatic Rings
0
Rotatable Bonds
98
Van der Waals Molecular Volume
2245.47
Topological Polar Surface Area
646.71
Hydrogen Bond Donors
18
Hydrogen Bond Acceptors
41
logP
24.63
Molar Refractivity
581.93
Admin
Created at
-
Updated at
10th May 2022