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CHEBI:84084 - 3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)

ChEBI IDCHEBI:84084
ChEBI Name3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)
Stars
ASCII Name3-PEA-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A)
DefinitionA lipid A derivative that consists of a linear trisaccharide phosphate comprising an L-glycero-α-D-manno-heptose residue phosphoethanolamine-substituted on O-3, another L-glycero-α-D-manno-heptose residue and a 3-deoxy-D-manno-oct-2-ulosonic acid (2-keto-3-deoxy-D-mannooctanoic acid, Kdo) in a (1→3), (1→5) sequence, with the Kdo residue at the reducing end connected via an α(2→6) linkage to a de-O-acylated lipid A. Corresponds to the de-O-acylated lipid A conjugate of the icsA mutant of the core oligosaccharide of Neisseria meningitidis.
Last Modified3 September 2015
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC120H227N4O53P5
Net Charge0
Average Mass2728.981
Monoisotopic Mass2727.38786
SMILES[H][C@]1([C@H](O)CO)O[C@@](OC[C@H]2O[C@@H](OC[C@H]3O[C@H](OP(=O)(O)OP(=O)(O)OCCN)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]3O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H]2OP(=O)(O)OP(=O)(O)O)(C(=O)O)C[C@@H](O)[C@H]1O[C@H]1O[C@]([H])([C@@H](O)CO)[C@@H](O)[C@H](O[C@H]2O[C@]([H])([C@@H](O)CO)[C@@H](O)[C@H](OP(=O)(O)OCCN)[C@@H]2O)[C@@H]1O
InChIInChI=1S/C120H227N4O53P5/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(137)163-86(66-60-54-48-42-35-29-23-17-11-5)76-98(139)167-112-100(124-94(135)75-85(65-59-53-47-41-34-28-22-16-10-4)162-95(136)67-61-55-49-43-36-30-24-18-12-6)115(158-81-91-101(140)111(166-97(138)74-84(129)64-58-52-46-40-33-27-21-15-9-3)99(116(164-91)175-182(156,157)177-180(152,153)161-72-70-122)123-93(134)73-83(128)63-57-51-45-39-32-26-20-14-8-2)165-92(110(112)173-181(154,155)176-178(147,148)149)82-159-120(119(145)146)77-87(130)108(109(172-120)90(133)80-127)170-117-104(143)113(102(141)106(168-117)88(131)78-125)171-118-105(144)114(174-179(150,151)160-71-69-121)103(142)107(169-118)89(132)79-126/h83-92,99-118,125-133,140-144H,7-82,121-122H2,1-6H3,(H,123,134)(H,124,135)(H,145,146)(H,150,151)(H,152,153)(H,154,155)(H,156,157)(H2,147,148,149)/t83-,84-,85-,86-,87-,88+,89+,90-,91-,92-,99-,100-,101-,102-,103-,104+,105+,106-,107-,108-,109-,110-,111-,112-,113+,114+,115-,116-,117-,118-,120-/m1/s1
InChIKeyXKWRWDCQEFNULL-CFDCENMDSA-N
ChEBI Ontology
Outgoing Relation(s)
3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a dodecanoate ester (CHEBI:87659)
3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a lipid As (CHEBI:25051)
3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a tetradecanoate ester (CHEBI:87691)
IUPAC Name 
(5R)-3-O-[(2-aminoethoxy)(hydroxy)phosphoryl]-5-[(1S)-1,2-dihydroxyethyl]-α-D-lyxopyranosyl-(1→3)-(5R)-5-[(1S)-1,2-dihydroxyethyl]-α-D-lyxopyranosyl-(1→5)-(6R)-3-deoxy-6-[(1R)-1,2-dihydroxyethyl]-β-L-erythro-hex-2-ulopyranonosyl-(2→6)-2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-[hydroxy(phosphonooxy)phosphoryl]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl-(1→6)-1-O-[{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-α-D-glucopyranose
Synonym  Source
3-PEA-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)ChEBI
Citations