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CHEBI:85677 - α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→4)-[α-Neup5Ac-(2→3)]-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid A

ChEBI IDCHEBI:85677
ChEBI Nameα-Neup5Ac-(2→3)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→4)-[α-Neup5Ac-(2→3)]-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid A
Stars
ASCII Namealpha-Neup5Ac-(2->3)-beta-D-Galp-(1->3)-beta-D-GalpNAc-(1->4)-[alpha-Neup5Ac-(2->3)]-beta-D-Galp-(1->3)-L-alpha-D-Hepp-(1->3)-[beta-D-Glcp-(1->4)]-L-alpha-D-Hepp6PEtn-(1->5)-[alpha-D-Kdo-(2->4)]-alpha-D-Kdo-(2->6)-lipid A
DefinitionA lipid A derivative in which an α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→3)-L-α-D-Hep-(1→3)-[β-D-Glc-(1→4)]-L-α-D-Hep6PEtn branched decasaccharide is linked (1→5) to a lipid A component containing four C14 and two C16 fatty acyl chains. Reported as a proposed lipooligosaccharide outer core structure of Campylobacter jejuni strains (CO016 and GC105) isolated from patients with Guillain-Barré syndrome (GBS) who had anti-GM1b antibodies, but neither anti-GM1 nor anti-GD1a antibodies (PMID:25867522).
Last Modified8 May 2015
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC179H319N6O90P3
Net Charge0
Average Mass4088.395
Monoisotopic Mass4085.97823
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]4[C@H](O[C@]5(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@]([H])([C@H](O)[C@H](O)CO)O5)[C@@H](O)[C@H](O[C@@H]5[C@H](O)[C@@H](O[C@@H]6[C@H](O)[C@@H](O[C@@H]7[C@H](O[C@]8(C(=O)O)C[C@@H](O)[C@@H](O)[C@@]([H])([C@H](O)CO)O8)C[C@](OC[C@H]8O[C@@H](OC[C@H]9O[C@H](OP(=O)(O)O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]9O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)[C@@H]8OP(=O)(O)O)(C(=O)O)O[C@]7([H])[C@H](O)CO)O[C@]([H])([C@H](CO)OP(=O)(O)OCCCN)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@]([H])([C@H](O)CO)[C@H]5O)O[C@@H]4CO)[C@@H]3NC(C)=O)[C@@H]2O)(C(=O)O)C[C@H](O)[C@H]1NC(C)=O
InChIInChI=1S/C179H319N6O90P3/c1-10-16-22-28-34-40-42-43-45-51-57-63-69-76-125(212)249-105(74-67-61-55-49-39-33-27-21-15-6)82-127(214)257-158-132(185-123(210)81-104(73-66-60-54-48-38-32-26-20-14-5)248-124(211)75-68-62-56-50-44-41-35-29-23-17-11-2)164(245-97-120-139(221)154(256-126(213)80-103(200)72-65-59-53-47-37-31-25-19-13-4)131(166(254-120)275-277(240,241)242)184-122(209)79-102(199)71-64-58-52-46-36-30-24-18-12-3)255-121(153(158)274-276(237,238)239)98-246-176(172(229)230)86-114(266-177(173(231)232)85-108(203)133(215)148(267-177)112(207)90-189)150(149(268-176)113(208)91-190)260-171-145(227)161(163(265-167-141(223)140(222)136(218)115(92-191)251-167)152(261-171)119(96-195)273-278(243,244)247-78-70-77-180)264-170-143(225)159(142(224)147(258-170)111(206)89-188)263-169-146(228)162(272-179(175(235)236)84-107(202)129(182-100(8)197)157(270-179)135(217)110(205)88-187)151(118(95-194)253-169)259-165-130(183-101(9)198)155(137(219)116(93-192)250-165)262-168-144(226)160(138(220)117(94-193)252-168)271-178(174(233)234)83-106(201)128(181-99(7)196)156(269-178)134(216)109(204)87-186/h102-121,128-171,186-195,199-208,215-228H,10-98,180H2,1-9H3,(H,181,196)(H,182,197)(H,183,198)(H,184,209)(H,185,210)(H,229,230)(H,231,232)(H,233,234)(H,235,236)(H,243,244)(H2,237,238,239)(H2,240,241,242)/t102-,103-,104-,105-,106+,107+,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119+,120-,121-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137+,138+,139-,140+,141-,142-,143+,144-,145+,146-,147-,148-,149-,150-,151+,152-,153-,154-,155-,156-,157-,158-,159+,160+,161-,162-,163-,164-,165+,166-,167+,168+,169+,170-,171+,176-,177-,178+,179+/m1/s1
InChIKeySJKUXTOFAPNBDP-ZPXRLOGZSA-N
ChEBI Ontology
Outgoing Relation(s)
α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→4)-[α-Neup5Ac-(2→3)]-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid A (CHEBI:85677) is a lipid As (CHEBI:25051)
IUPAC Name 
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→4)]-β-D-galactopyranosyl-(1→3)-D-glycero-α-D-manno-heptopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-6-O-[(3-aminopropoxy)(hydroxy)phosphoryl]-L-glycero-α-D-manno-heptopyranosyl-(1→5)-[3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→4)]-3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→6)-2-deoxy-3-O-[(3R)-3-(hexadecanoyloxy)tetradecanoyl]-2-{[(3R)-3-(hexadecanoyloxy)tetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl-(1→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose
Synonyms  Source
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulonosyl-(2→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulonosyl-(2→3)-β-D-galactosyl-(1→3)-2-acetamido-2-deoxy-β-D-galactosyl-(1→4)]-β-D-galactosyl-(1→3)-D-glycero-α-D-manno-heptosyl-(1→3)-[β-D-glucosyl-(1→4)]-6-O-[(3-aminopropoxy)(hydroxy)phosphoryl]-L-glycero-α-D-manno-heptosyl-(1→5)-[3-deoxy-α-D-manno-oct-2-ulonosyl-(2→4)]-3-deoxy-α-D-manno-oct-2-ulonosyl-(2→6)-2-deoxy-3-O-[(3R)-3-(hexadecanoyloxy)tetradecanoyl]-2-{[(3R)-3-(hexadecanoyloxy)tetradecanoyl]amino}-4-O-phosphono-β-D-glucosyl-(1→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucoseChEBI
α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→3)-L-α-D-Hep-(1→3)-[β-D-Glc-(1→4)]-L-α-D-Hep6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid AChEBI
α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→4)-[α-Neup5Ac-(2→3)]-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid A (C. jejuni)ChEBI
α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→3)-L-α-D-Hep-(1→3)-[β-D-Glc-(1→4)]-L-α-D-Hep6PEtn-(1→5)-[α-D-Kdo-(2→4)]-α-D-Kdo-(2→6)-lipid A (C. jejuni)ChEBI
Citations