alpha-Neup5Ac-(2->8)-alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->3)-L-alpha-D-Hepp-(1->3)-[beta-D-Glcp-(1->4)]-L-alpha-D-Hepp-(1->5)-[alpha-Kdo-(2->4)]-alpha-Kdo (CHEBI:167384)

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CHEBI:167384 - α-Neup5Ac-(2→8)-α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[α-Kdo-(2→4)]-α-Kdo

ChEBI ID	CHEBI:167384
ChEBI Name	α-Neup5Ac-(2→8)-α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[α-Kdo-(2→4)]-α-Kdo
Stars
ASCII Name	alpha-Neup5Ac-(2->8)-alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->3)-L-alpha-D-Hepp-(1->3)-[beta-D-Glcp-(1->4)]-L-alpha-D-Hepp-(1->5)-[alpha-Kdo-(2->4)]-alpha-Kdo
Definition	A branched amino octasaccharide consisting of a linear hexasaccharide comprising two N-acetyl-α-neuraminic acid residues, a β-D-galactose residue, two L-glycero-α-D-manno-heptose (L-α-D-Hep) residues and a 3-deoxy-α-D-manno-oct-2-ulose (α-Kdo) residue linked in sequence (2→8), (2→3), (1→3),(1→3), (1→3) and (1→5), to the L-α-D-Hep residue proximal to the reducing end is also linked (1→4) a β-D-glucose residue, while the α-Kdo residue also carries a second α-Kdo residue linked (2→-4). One of a number of chemoenzymatically synthesised oligosaccharides composed of the inner core oligosaccharide of Campylobacter jejuni extended by various ganglioside mimics.
Last Modified	27 January 2021
Submitter	Marcus Ennis
Downloads	Molfile

Formula	C64H104N2O53
Net Charge	0
Average Mass	1749.497
Monoisotopic Mass	1748.55043
SMILES	[H][C@]1([C@H](O)CO)O[C@@](O[C@@H]2C[C@](O)(C(=O)O)O[C@]([H])([C@H](O)CO)[C@@H]2O[C@H]2O[C@]([H])([C@@H](O)CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O[C@H]3O[C@]([H])([C@@H](O)CO)[C@@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O[C@]5(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@@H](CO)O[C@]6(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O6)O5)[C@H]4O)[C@@H]3O)[C@@H]2O)(C(=O)O)C[C@@H](O)[C@H]1O
InChI	InChI=1S/C64H104N2O53/c1-15(75)65-29-17(77)3-62(58(98)99,117-47(29)32(86)20(80)7-67)114-28(14-74)35(89)48-30(66-16(2)76)18(78)4-64(118-48,60(102)103)119-50-34(88)27(13-73)106-54(40(50)94)110-49-38(92)42(21(81)8-68)107-55(39(49)93)111-51-41(95)56(108-44(23(83)10-70)52(51)112-53-37(91)36(90)33(87)26(12-72)105-53)109-46-25(6-61(104,57(96)97)115-45(46)24(84)11-71)113-63(59(100)101)5-19(79)31(85)43(116-63)22(82)9-69/h17-56,67-74,77-95,104H,3-14H2,1-2H3,(H,65,75)(H,66,76)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t17-,18-,19+,20+,21-,22+,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,36-,37+,38+,39-,40+,41-,42+,43+,44+,45+,46+,47+,48+,49-,50-,51+,52+,53-,54-,55+,56+,61+,62+,63+,64-/m0/s1
InChIKey	VJCUUTHFHVSROB-YKIXFZKNSA-N

ChEBI Ontology

Outgoing Relation(s)
	α-Neup5Ac-(2→8)-α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[α-Kdo-(2→4)]-α-Kdo (CHEBI:167384) is a amino octasaccharide (CHEBI:71060)

IUPAC Name
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→8)-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→3)-L-glycero-α-D-manno-heptopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-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-ulopyranosonic acid

IUPAC Name

5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→8)-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→3)-L-glycero-α-D-manno-heptopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-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-ulopyranosonic acid

Synonyms	Source
Neu5Acα2-8Neu5Acα2-3Galβ1-3Hepα1-3(Glcβ1-4)Hepα1-5(Kdoα2-4)Kdoα	ChEBI
α-Kdo-(2→4)-[α-Neup5Ac-(2→8)-α-Neup5Ac-(2→3)-β-D-Galp-(1→3)-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)]-α-Kdo	ChEBI
α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-L-α-D-Hep-(1→3)-[β-D-Glc-(1→4)]-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo	ChEBI

Citations