EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:150019 - 3-{β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol

ChEBI IDCHEBI:150019
ChEBI Name3-{β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol
Stars
ASCII Name3-{beta-D-GlcNAc-(1->3)-[D-GrO-(2->1)]-beta-D-GlcNAc-(6-P-6)-beta-D-GlcNAc-(1->3)-[D-GrO-(2->1)]-beta-D-GlcNAc-(6-P-6)-beta-D-GlcNAc-(1->3)-[D-GrO-(2->1)]-beta-D-GlcNAc-(6-P-6)-beta-D-Glc-(1->6)-beta-D-Glc-(1->6)-beta-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol
DefinitionA glycosylglycerol derivative in which the glycosyl moiety of glycosyl-sn-glycerol is N-acetyl-β-D-glucosaminyl-(1→3)-[(D-glyceric acid)-(2→1)]-β-D-glucosaminyl-(6-phospho-6)-N-acetyl-β-D-glucosaminyl-(1→3)-[(D-glyceric acid)-(2→1)]-β-D-glucosaminyl-(6-phospho-6)-N-acetyl-β-D-glucosaminyl-(1→3)-[(D-glyceric acid)-(2→1)]-β-D-glucosaminyl-(6-phospho-6)-β-D-glucosyl-(1→6)-β-D-glucosyl-(1→6)-β-D-glucosyl attached at O-3, with O-1 and O-2 both carrying myristoyl substituents. Synthetic C. difficile lipoteichoic acid (LTA) molecule consisting of lipid + core region and three [(→6)-α-D-GlcpNAc-(1→3)-[P-6]-α-D-GlcpNAc-(1→2)-D-GroA polymeric repeats (where P-6 is a phosphodiester bridge and GroA is glyceric acid).
Last Modified22 August 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC106H183N6O68P3
Net Charge0
Average Mass2722.526
Monoisotopic Mass2721.02590
SMILESCCCCCCCCCCCCCC(=O)OC[C@H](CO[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO[C@@H]3O[C@H](COP(=O)(O)OC[C@H]4O[C@H](O[C@H](CO)C(=O)O)[C@H](NC(C)=O)[C@@H](O[C@H]5O[C@H](COP(=O)(O)OC[C@H]6O[C@H](O[C@H](CO)C(=O)O)[C@H](NC(C)=O)[C@@H](O[C@H]7O[C@H](COP(=O)(O)OC[C@H]8O[C@H](O[C@H](CO)C(=O)O)[C@H](NC(C)=O)[C@@H](O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9NC(C)=O)[C@@H]8O)[C@@H](O)[C@H](O)[C@H]7NC(C)=O)[C@@H]6O)[C@@H](O)[C@H](O)[C@H]5NC(C)=O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)CCCCCCCCCCCCC
InChIInChI=1S/C106H183N6O68P3/c1-9-11-13-15-17-19-21-23-25-27-29-31-66(123)155-37-53(165-67(124)32-30-28-26-24-22-20-18-16-14-12-10-2)38-156-104-89(140)86(137)77(128)58(175-104)39-157-105-90(141)87(138)78(129)59(176-105)40-158-106-91(142)88(139)79(130)62(177-106)43-161-183(153,154)164-46-65-82(133)94(73(112-52(8)122)103(174-65)169-57(36-116)97(147)148)180-100-70(109-49(5)119)85(136)76(127)61(171-100)42-160-182(151,152)163-45-64-81(132)93(72(111-51(7)121)102(173-64)168-56(35-115)96(145)146)179-99-69(108-48(4)118)84(135)75(126)60(170-99)41-159-181(149,150)162-44-63-80(131)92(71(110-50(6)120)101(172-63)167-55(34-114)95(143)144)178-98-68(107-47(3)117)83(134)74(125)54(33-113)166-98/h53-65,68-94,98-106,113-116,125-142H,9-46H2,1-8H3,(H,107,117)(H,108,118)(H,109,119)(H,110,120)(H,111,121)(H,112,122)(H,143,144)(H,145,146)(H,147,148)(H,149,150)(H,151,152)(H,153,154)/t53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,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-,98-,99-,100-,101+,102+,103+,104-,105-,106-/m1/s1
InChIKeyANLTUYVHGYLHIW-WOAOQVJYSA-N
Species of MetaboliteComponentSourceComments
Clostridioides difficile (ncbitaxon:1496) - PubMed (32191024) Synthetic lipoteichoic acid molecule
ChEBI Ontology
Outgoing Relation(s)
3-{β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150019) has functional parent 1,2-ditetradecanoyl-sn-glycerol (CHEBI:80651)
3-{β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150019) is a glycosylglycerol derivative (CHEBI:63427)
3-{β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-GlcNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcNAc-(6-P-6)-β-D-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150019) is a lipoteichoic acid (CHEBI:28640)
IUPAC Name 
3-{2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-[(1S)-1-carboxy-2-hydroxyethyl-(1→1)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(6-phospho-6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-[(1S)-1-carboxy-2-hydroxyethyl-(1→1)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(6-phospho-6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-[(1S)-1-carboxy-2-hydroxyethyl-(1→1)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(6-phospho-6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl}-1,2-bis(tetradecanoyloxy)-sn-glycerol
Synonyms  Source
WH237ChEBI
3-{β-D-GlcpNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcpNAc-(6-P-6)-β-D-GlcpNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcpNAc-(6-P-6)-β-D-GlcpNAc-(1→3)-[D-GrO-(2→1)]-β-D-GlcpNAc-(6-P-6)-β-D-Glcp-(1→6)-β-D-Glcp-(1→6)-β-D-Glcp-yl}-1,2-dimyristoyl-sn-glycerolChEBI
(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4-{[(2S,3R,4R,5S,6R)-3-acetamido-6-({[({(2R,3S,4R,5R,6R)-5-acetamido-4-{[(2S,3R,4R,5S,6R)-3-acetamido-6-({[({(2R,3S,4R,5R,6R)-5-acetamido-4-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-[(1R)-1-carboxy-2-hydroxyethoxy]-3-hydroxytetrahydro-2H-pyran-2-yl}methoxy)(hydroxy)phosphoryl]oxy}methyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6-[(1R)-1-carboxy-2-hydroxyethoxy]-3-hydroxytetrahydro-2H-pyran-2-yl}methoxy)(hydroxy)phosphoryl]oxy}methyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6-({[{[(2R,3S,4S,5R,6R)-6-{[(2R,3S,4S,5R,6R)-6-({(2R,3S,4S,5R,6R)-6-[(2S)-2,3-bis(tetradecanoyloxy)propoxy]-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl}methoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]methoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}methyl)-5-hydroxytetrahydro-2H-pyran-2-yl]oxy}-3-hydroxypropanoic acidIUPAC
Citations