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CHEBI:59384 - α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→2)-α-L-Rhap

ChEBI IDCHEBI:59384
ChEBI Nameα-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→2)-α-L-Rhap
Stars
ASCII Namealpha-L-Rhap-(1->3)-[alpha-D-Glcp-(1->4)]-alpha-L-Rhap-(1->3)-beta-D-GlcpNAc-(1->2)-alpha-L-Rhap
DefinitionA branched amino pentasaccharide consisting of a tetrasaccharide chain of α-D-glucose, α-L-rhamnose, N-acetyl-β-D-glucosamine and α-L-rhamnose residues linked sequentially (1→4), (1→3) and (1→2), to the non-reducing rhamnose residue of which is also linked (1→3) a further α-L-rhamnose residue. Derived from the Shigella liposaccharide O-antigen, it shows antigenic properties.
Last Modified28 September 2016
Submitterzjosephs
DownloadsMolfile
FormulaC32H55NO23
Net Charge0
Average Mass821.776
Monoisotopic Mass821.31649
SMILESCC(=O)N[C@H]1[C@H](O[C@@H]2[C@H](O)[C@@H](O)[C@H](C)O[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@@H](C)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O
InChIInChI=1S/C32H55NO23/c1-7-15(38)20(43)27(28(47)48-7)56-29-13(33-10(4)36)25(17(40)12(6-35)51-29)54-32-23(46)26(55-30-21(44)18(41)14(37)8(2)49-30)24(9(3)50-32)53-31-22(45)19(42)16(39)11(5-34)52-31/h7-9,11-32,34-35,37-47H,5-6H2,1-4H3,(H,33,36)/t7-,8-,9-,11+,12+,13+,14-,15-,16+,17+,18+,19-,20+,21+,22+,23+,24-,25+,26-,27+,28+,29-,30-,31+,32-/m0/s1
InChIKeyRCPQNVAYNPZLHX-PNYKSLIESA-N
Roles Classification
Biological Role:
antigen  Any substance that stimulates an immune response in the body, such as through antibody production or by presentation to a T-cell receptor after binding to a major histocompability complex (MHC).
ChEBI Ontology
Outgoing Relation(s)
α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→2)-α-L-Rhap (CHEBI:59384) has role antigen (CHEBI:59132)
α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→2)-α-L-Rhap (CHEBI:59384) is a amino pentasaccharide (CHEBI:59268)
IUPAC Name 
α-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranose
Synonyms  Source
6-deoxy-α-L-mannopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-6-deoxy-α-L-mannopyranoseChEBI
α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoseIUPAC
B(E)CDAChEBI
α-L-Rha-(1→3)-[α-D-Glc-(1→4)]-α-L-Rha-(1→3)-β-D-GlcNAc-(1→2)-α-L-RhaChEBI
α-L-rhamnosyl-(1→3)-[α-D-glucosyl-(1→4)]-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→2)-α-L-rhamnoseChEBI
Rhaα1-3(Glcα1-4)Rhaα1-3GlcNAcβ1-2RhaαChEBI
Citations