Structure database (LMSD)

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LM IDLMSL01050001
Common NameBordetella pertussis lipid A
Systematic Name-
Synonyms-
Exact Mass
1558.9897 (neutral)    Calculate m/z:
FormulaC78H148N2O24P2
CategorySaccharolipids [SL]
Main ClassAcylaminosugars [SL01]
Sub ClassPentaacylaminosugars [SL0105]
PubChem CID42608337
InChIKeyDHSXJMRVJPCQHY-GMAIUFEFSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C78H148N2O24P2/c1-6-11-16-21-25-29-30-34-38-43-48-53-68(87)98-63(52-47-
42-37-33-28-24-19-14-9-4)57-67(86)80-72-76(102-70(89)56-62(84)51-46-41-36-32-27-
23-18-13-8-3)74(103-105(91,92)93)64(58-81)99-77(72)97-59-65-73(90)75(101-69(88)5
5-61(83)50-44-39-20-15-10-5)71(78(100-65)104-106(94,95)96)79-66(85)54-60(82)49-4
5-40-35-31-26-22-17-12-7-2/h60-65,71-78,81-84,90H,6-59H2,1-5H3,(H,79,85)(H,80,86
)(H2,91,92,93)(H2,94,95,96)/t60?,61?,62?,63?,64?,65?,71-,72-,73+,74+,75?,76?,77+
,78+/m0/s1
SMILESO1C(CO[C@H]2[C@H](C(OC(=O)CC(O)CCCCCCCCCCC)[C@H](OP(=O)(O)O)C(CO)O2)NC(=O)CC(OC(
=O)CCCCCCCCCCCCC)CCCCCCCCCCC)[C@@H](O)C([C@H](NC(=O)CC(O)CCCCCCCCCCC)[C@H]1OP(O)
(=O)O)OC(=O)CC(O)CCCCCCC
StatusActive
ReferencesStructural characterization of Bordetella parapertussis lipid A. El Hamidi A, Novikov A, Karibian D, Perry MB, Caroff M. J Lipid Res. 2009 May;50(5):854-9
Calculated physicochemical properties (?):
 Heavy Atoms106Rings2Aromatic Rings0Rotatable Bonds72
 van der Waals
Molecular Volume
1592.66Topological Polar
Surface Area
403.60Hydrogen
Bond Donors
11Hydrogen
Bond Acceptors
24
 logP19.83Molar
Refractivity
413.99