Structure database (LMSD)

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LM IDLMSL01060002
Common NameNeisseria meningitidis lipid A
Systematic Name-
Synonyms-
Exact Mass
1713.1255 (neutral)    Calculate m/z:
FormulaC88H166N2O25P2
CategorySaccharolipids [SL]
Main ClassAcylaminosugars [SL01]
Sub ClassHexaacylaminosugars [SL0106]
PubChem CID24774162
InChIKeySWRJHGCTVNUMIJ-JBCGXEBKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C88H166N2O25P2/c1-7-13-19-25-31-35-41-47-53-59-71(108-77(96)61-55-49-43-37-33-27-21-15-9-3)65-75(94)89-81-85(112-79(98)63-69(92)57-51-45-39-29-23-17-11-5)83(100)74(111-88(81)115-117(104,105)106)68-107-87-82(86(84(73(67-91)110-87)114-116(101,102)103)113-80(99)64-70(93)58-52-46-40-30-24-18-12-6)90-76(95)66-72(60-54-48-42-36-32-26-20-14-8-2)109-78(97)62-56-50-44-38-34-28-22-16-10-4/h69-74,81-88,91-93,100H,7-68H2,1-6H3,(H,89,94)(H,90,95)(H2,101,102,103)(H2,104,105,106)/t69-,70-,71-,72-,73-,74-,81-,82-,83-,84-,85-,86-,87-,88-/m1/s1
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SMILES
O(P(O)(=O)O)[C@@H]1[C@H](NC(=O)C[C@H](OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCC)[C@H](O)[C@@H](CO[C@H]2[C@H](NC(=O)C[C@H](OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCC)[C@H](OP(O)(O)=O)[C@@H](CO)O2)O1
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StatusActive
ReferencesThe Role of Carbohydrates in the Lipopolysaccharide (LPS)/Toll-Like Receptor 4 (TLR4) Signalling
Int J Mol Sci. 2017
DOI: 10.3390/ijms18112318
PMID: 29099761
Calculated physicochemical properties (?):
 Heavy Atoms117Rings2Aromatic Rings0Rotatable Bonds82
 van der Waals
Molecular Volume
1771.81Topological Polar
Surface Area
409.67Hydrogen
Bond Donors
10Hydrogen
Bond Acceptors
27
 logP23.52Molar
Refractivity
460.47