Structure database (LMSD)

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LM IDLMSL01060003
Common NameEscherichia coli lipid A
Systematic Name-
Synonyms-
Exact Mass
1797.2194 (neutral)    Calculate m/z:
FormulaC94H178N2O25P2
CategorySaccharolipids [SL]
Main ClassAcylaminosugars [SL01]
Sub ClassHexaacylaminosugars [SL0106]
PubChem CID9877306
HMDB IDHMDB0013244
CHEBI ID134256
InChIKeyGZQKNULLWNGMCW-PWQABINMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1
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SMILES
O(P(O)(=O)O)[C@@H]1[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[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](OC(=O)CCCCCCCCCCCCC)CCCCCCCCCCC)[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 Atoms123Rings2Aromatic Rings0Rotatable Bonds88
 van der Waals
Molecular Volume
1875.61Topological Polar
Surface Area
409.67Hydrogen
Bond Donors
10Hydrogen
Bond Acceptors
27
 logP25.86Molar
Refractivity
488.17