Structure database (LMSD)

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LM IDLMSL01050004
Common NameRhodobacter sphaeroides Lipid A
Systematic Name-
Synonyms-
Exact Mass
1526.9271 (neutral)    Calculate m/z:
FormulaC76H140N2O24P2
CategorySaccharolipids [SL]
Main ClassAcylaminosugars [SL01]
Sub ClassPentaacylaminosugars [SL0105]
PubChem CID-
InChIKeyCCKKFUQFWHEHKD-DTSHGSGKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C76H140N2O24P2/c1-6-11-16-21-25-28-29-32-36-41-46-51-66(85)96-61(50-45-40-35-31-27-23-18-13-8-3)55-65(84)78-70-74(100-68(87)54-60(82)48-42-37-20-15-10-5)72(101-103(89,90)91)62(56-79)97-75(70)95-57-63-71(88)73(99-67(86)53-59(81)49-44-38-33-24-19-14-9-4)69(76(98-63)102-104(92,93)94)77-64(83)52-58(80)47-43-39-34-30-26-22-17-12-7-2/h28-29,59-63,69-76,79,81-82,88H,6-27,30-57H2,1-5H3,(H,77,83)(H,78,84)(H2,89,90,91)(H2,92,93,94)/b29-28-/t59-,60-,61-,62-,63-,69-,70-,71-,72-,73-,74-,75-,76-/m1/s1
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SMILES
O(P(O)(=O)O)[C@@H]1[C@H](NC(=O)CC(=O)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(CCCCC/C=C\CCCCCC)=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCC)[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 Atoms104Rings2Aromatic Rings0Rotatable Bonds69
 van der Waals
Molecular Volume
1552.78Topological Polar
Surface Area
400.44Hydrogen
Bond Donors
10Hydrogen
Bond Acceptors
26
 logP18.74Molar
Refractivity
403.15