Structure Database (LMSD)

Common Name
Kdo2-lipid A
Systematic Name
Kdo2-lipid A
Synonyms
LM ID
LMSL02000001
Status
Active
Exact Mass
Calculate m/z
2237.336009
Formula



Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

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.

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
Pubmed ID: 16479018

Other Databases

CHEBI ID
PubChem CID

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