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CHEBI:150014 - 3-{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:150014
ChEBI Name3-{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-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)-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 one [(→6)-α-D-GlcpNAc-(1→3)-[P-6]-α-D-GlcpNAc-(1→2)-D-GroA polymeric repeat (where P-6 is a phosphodiester bridge and GroA is glyceric acid).
Last Modified22 August 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC68H121N2O36P
Net Charge0
Average Mass1573.668
Monoisotopic Mass1572.74366
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](CO)[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/C68H121N2O36P/c1-5-7-9-11-13-15-17-19-21-23-25-27-46(75)93-31-39(99-47(76)28-26-24-22-20-18-16-14-12-10-8-6-2)32-94-66-59(86)56(83)51(78)42(103-66)33-95-67-60(87)57(84)52(79)43(104-67)34-96-68-61(88)58(85)53(80)44(105-68)35-97-107(91,92)98-36-45-54(81)62(49(70-38(4)74)65(102-45)101-41(30-72)63(89)90)106-64-48(69-37(3)73)55(82)50(77)40(29-71)100-64/h39-45,48-62,64-68,71-72,77-88H,5-36H2,1-4H3,(H,69,73)(H,70,74)(H,89,90)(H,91,92)/t39-,40-,41-,42-,43-,44-,45-,48-,49-,50-,51-,52-,53-,54-,55-,56+,57+,58+,59-,60-,61-,62-,64-,65+,66-,67-,68-/m1/s1
InChIKeyKRGZFBLYDAOILK-CVYHBHJLSA-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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150014) 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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150014) is a glycosylglycerol derivative (CHEBI:63427)
3-{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:150014) 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→6)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl}-1,2-bis(tetradecanoyloxy)-sn-glycerol
Synonyms  Source
(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-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
3-{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
WH235ChEBI
Citations