alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glc-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNacO[CH(2)](2)NH(2) (CHEBI:194247)

ChEBI > Main

CHEBI:194247 - α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glc-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNacO[CH₂]₂NH₂

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ChEBI Name	α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glc-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNacO[CH₂]₂NH₂

ChEBI ID	CHEBI:194247

ChEBI ASCII Name	alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glc-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNacO[CH2]2NH2

Definition	A synthetic β-D-glucoside that is a branched pentadecasaccharide derivative consisting of three β-D-Glc-(1→6)-[α-L-Rha-(1→3)]-α-D-Glc-(1→3)-α-L-Rha2Ac-(1→3)-β-D-GlcNAc pentasaccharide units linked (1→4) between the GlcNac residue at the reducing end of one unit and the OH at position 4 of the α-D-glucose residue of the adjacent unit. An aminoethyl linker from the reducing-end GlcNAc residue allows for efficient conjugation to a carrier protein.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C104H172N4O73

Net Charge

Average Mass

2646.475

Monoisotopic Mass

2644.98697

InChI

InChI=1S/C104H172N4O73/c1-24-48(121)61(134)70(143)96(153-24)176-81-60(133)42(21-150-93-67(140)64(137)54(127)36(15-109)165-93)168-99(73(81)146)177-82-51(124)27(4)157-103(87(82)159-33(10)118)174-79-46(107-31(8)116)91(163-40(19-113)58(79)131)171-77-44(23-152-95-69(142)66(139)56(129)38(17-111)167-95)170-101(75(148)86(77)181-98-72(145)63(136)50(123)26(3)155-98)179-84-53(126)29(6)158-104(89(84)161-35(12)120)175-80-47(108-32(9)117)92(164-41(20-114)59(80)132)172-76-43(22-151-94-68(141)65(138)55(128)37(16-110)166-94)169-100(74(147)85(76)180-97-71(144)62(135)49(122)25(2)154-97)178-83-52(125)28(5)156-102(88(83)160-34(11)119)173-78-45(106-30(7)115)90(149-14-13-105)162-39(18-112)57(78)130/h24-29,36-104,109-114,121-148H,13-23,105H2,1-12H3,(H,106,115)(H,107,116)(H,108,117)/t24-,25-,26-,27-,28-,29-,36+,37+,38+,39+,40+,41+,42+,43+,44+,45+,46+,47+,48-,49-,50-,51-,52-,53-,54+,55+,56+,57+,58+,59+,60+,61+,62+,63+,64-,65-,66-,67+,68+,69+,70+,71+,72+,73+,74+,75+,76+,77+,78+,79+,80+,81-,82+,83+,84+,85+,86+,87+,88+,89+,90+,91-,92-,93+,94+,95+,96-,97-,98-,99+,100+,101+,102-,103-,104-/m0/s1

InChIKey

SIDJCNYNJQOQAR-WJMQBRDPSA-N

SMILES

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O[C@H](O[C@@H]3[C@@H](O)[C@H](C)O[C@@H](O[C@H]4[C@H](O)[C@@H](CO)O[C@@H](O[C@@H]5[C@@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@H](O[C@@H]6[C@@H](O)[C@H](C)O[C@@H](O[C@H]7[C@H](O)[C@@H](CO)O[C@@H](O[C@@H]8[C@@H](CO[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)O[C@H](O[C@@H]9[C@@H](O)[C@H](C)O[C@@H](O[C@H]%10[C@H](O)[C@@H](CO)O[C@@H](OCCN)[C@@H]%10NC(C)=O)[C@@H]9OC(C)=O)[C@H](O)[C@H]8O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@@H]7NC(C)=O)[C@@H]6OC(C)=O)[C@H](O)[C@H]5O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H]4NC(C)=O)[C@@H]3OC(C)=O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Roles Classification
Biological Role(s):	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). (via alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[alpha-L-Rhap-(1->3)-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glc-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNAc-(1->4)]-[beta-D-Glcp-(1->6)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNacO[CH2]2NH2 )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glc-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNacO[CH₂]₂NH₂ (CHEBI:194247) has role antigen (CHEBI:59132) α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[α-L-Rhap-(1→3)-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glc-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAc-(1→4)]-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNacO[CH₂]₂NH₂ (CHEBI:194247) is a β-D-glucoside (CHEBI:22798)

IUPAC Name

2-aminoethyl α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside

Synonyms	Sources
2-aminoethyl 6-deoxy-α-L-mannopyranosyl-(1→3)-[6-deoxy-α-L-mannopyranosyl-(1→3)-[6-deoxy-α-L-mannopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside	IUPAC
2-aminoethyl α-L-rhamnosyl-(1→3)-[α-L-rhamnosyl-(1→3)-[α-L-rhamnosyl-(1→3)-[β-D-glucosyl-(1→6)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→4)]-[β-D-glucosyl-(1→6)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→4)]-[β-D-glucosyl-(1→6)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminide	ChEBI
2-aminoethyl β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→3)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[α-L-rhamnopyranosyl-(1→3)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-[α-L-rhamnopyranosyl-(1→3)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside	ChEBI
2-aminoethyl β-D-glucosyl-(1→6)-[β-D-glucosyl-(1→6)-[β-D-glucosyl-(1→6)-[α-L-rhamnosyl-(1→3)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→4)]-[α-L-rhamnosyl-(1→3)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→4)]-[α-L-rhamnosyl-(1→3)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminide	ChEBI
α-L-Rha-(1→3)-[α-L-Rha-(1→3)-[α-L-Rha-(1→3)-[β-D-Glc-(1→6)]-α-D-Glc-(1→3)-α-L-Rha2Ac-(1→3)-GlcNAc-(1→4)]-[β-D-Glc-(1→6)]-α-D-Glc-(1→3)-α-L-Rha2Ac-(1→3)-β-D-GlcNAc-(1→4)]-[β-D-Glc-(1→6)]-α-D-Glc-(1→3)-α-L-Rha2Ac-(1→3)-β-D-GlcNacO[CH₂]₂NH₂	ChEBI
Glcβ1-6[Glcβ1-6[Glcβ1-6(Rhaα1-3)Glcα1-3Rhaα2Ac1-3GlcNAcβ1-4](Rhaα1-3)Glcα1-3Rha2Acα1-3GlcNAcβ1-4](Rhaα1-3)Glcα1-3Rhaα1-3GlcNAcβO[CH₂]₂NH₂	ChEBI
Rhaα1-3[Rhaα1-3[Rhaα1-3(Glcβ1-6)Glcα1-3Rha2Acα1-3GlcNAc1-4](Glcβ1-6)Glcα1-3Rha2Ac1-3GlcNAcβ1-4](Glcβ1-6)Glcα1-3Rha2Ac1-3GlcNAcβO[CH₂]₂NH₂	IUPAC

Citation	Type	Source
36186572	PubMed citation	Europe PMC

Last Modified

20 January 2023

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