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CHEBI:146807 - β1,4-GalNAc-disialyl-Lc4

Default Structure
ChEBI IDCHEBI:146807
ChEBI Nameβ1,4-GalNAc-disialyl-Lc4
Stars
ASCII Namebeta1,4-GalNAc-disialyl-Lc4
DefinitionAn amino heptasaccharide consisting of a β-D-Gal-(1→3)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-Glc tetrasaccharide backbone, to the galactosyl residue distal to the reducing end is (1→4)-linked a β-DGlcNAc residue, while Neu5Ac residues are linked to this same galactosyl residue and the GlcNAc residue via (2→3) and (2→6) glycosidic linkages respectively. An antigen for the monoclonal antibody RM2, it is used as a histological marker for prostate cancer.
Last Modified15 March 2022
SubmitterGareth Owen
DownloadsMolfile
FormulaC56H92N4O42
Net Charge0
Average Mass1493.338
Monoisotopic Mass1492.51861
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@](OC[C@H]2O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@H](O)O[C@@H]4CO)[C@@H]3O)[C@H](NC(C)=O)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H](O[C@]4(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@]([H])([C@H](O)[C@H](O)CO)O4)[C@H]3O)[C@@H]2O)(C(=O)O)C[C@H](O)[C@H]1NC(C)=O
WURCSWURCS=2.0/5,7,6/[a2122h-1b_1-5][a2112h-1b_1-5][a2122h-1b_1-5_2*NCC/3=O][Aad21122h-2a_2-6_5*NCC/3=O][a2112h-1b_1-5_2*NCC/3=O]/1-2-3-2-4-5-4/a4-b1_b3-c1_c3-d1_c6-g2_d3-e2_d4-f1
InChIInChI=1S/C56H92N4O42/c1-14(67)57-27-18(71)5-55(53(86)87,100-44(27)31(75)20(73)7-61)90-13-26-35(79)43(30(60-17(4)70)50(95-26)99-46-34(78)23(10-64)93-51(39(46)83)96-41-24(11-65)91-48(85)38(82)37(41)81)98-52-40(84)47(42(25(12-66)94-52)97-49-29(59-16(3)69)36(80)33(77)22(9-63)92-49)102-56(54(88)89)6-19(72)28(58-15(2)68)45(101-56)32(76)21(74)8-62/h18-52,61-66,71-85H,5-13H2,1-4H3,(H,57,67)(H,58,68)(H,59,69)(H,60,70)(H,86,87)(H,88,89)/t18-,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-,55+,56-/m0/s1
InChIKeyADHYCSCAYMZNRY-ALFFWPGUSA-N
ChEBI Ontology
Outgoing Relation(s)
β1,4-GalNAc-disialyl-Lc4 (CHEBI:146807) is a amino heptasaccharide (CHEBI:70970)
β1,4-GalNAc-disialyl-Lc4 (CHEBI:146807) is a neuraminic acids (CHEBI:25508)
IUPAC Name 
2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→4)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)]-β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose
Synonyms  Source
(2R,4S,5R,6R)-5-Acetamido-2-[[(2R,3S,4R,5R,6S)-5-acetamido-4-[(2R,3R,4R,5S,6R)-4-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-3-hydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidIUPAC
5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2→3)-[2-acetamido-2-deoxy-beta-D-galacto-hexopyranosyl-(1→4)]-beta-D-galacto-hexopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2→6)]-2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1→3)-beta-D-galacto-hexopyranosyl-(1→4)-beta-D-gluco-hexopyranoseSUBMITTER
NeuAc(a2-3)[GalNAc(b1-4)]Gal(b1-3)[NeuAc(a2-6)]GlcNAc(b1-3)Gal(b1-4)b-GlcSUBMITTER
NeuAcα2-3(GalNAcβ1-4)Galβ1-3(NeuAcα2-6)GlcNAcβ1-3Galβ1-4GlcβIUPAC
RM2 antigenChEBI
β-DGlcpNAc-(1→4)-[α-Neup5Ac-(2→3)]-β-D-Galp-(1→3)-[α-Neup5Ac-(2→6)]-β-DGlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-GlcpIUPAC
Manual XrefsDatabases
G00189KEGG GLYCAN
G08324IQGlyTouCan
Citations