3-{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 (CHEBI:150017)

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CHEBI:150017 - 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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol

ChEBI ID	CHEBI:150017
ChEBI Name	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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol
Stars
ASCII Name	3-{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
Definition	A 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)-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 two [(→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 Modified	22 August 2023
Submitter	Marcus Ennis
Downloads	Molfile

Formula	C87H152N4O52P2
Net Charge	0
Average Mass	2148.097
Monoisotopic Mass	2146.88478
SMILES	CCCCCCCCCCCCCC(=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](CO)[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
InChI	InChI=1S/C87H152N4O52P2/c1-7-9-11-13-15-17-19-21-23-25-27-29-56(99)124-34-46(132-57(100)30-28-26-24-22-20-18-16-14-12-10-8-2)35-125-85-74(113)71(110)64(103)50(139-85)36-126-86-75(114)72(111)65(104)51(140-86)37-127-87-76(115)73(112)66(105)53(141-87)39-129-145(122,123)131-41-55-68(107)78(61(91-45(6)98)84(138-55)135-49(33-94)80(118)119)143-82-59(89-43(4)96)70(109)63(102)52(136-82)38-128-144(120,121)130-40-54-67(106)77(60(90-44(5)97)83(137-54)134-48(32-93)79(116)117)142-81-58(88-42(3)95)69(108)62(101)47(31-92)133-81/h46-55,58-78,81-87,92-94,101-115H,7-41H2,1-6H3,(H,88,95)(H,89,96)(H,90,97)(H,91,98)(H,116,117)(H,118,119)(H,120,121)(H,122,123)/t46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71+,72+,73+,74-,75-,76-,77-,78-,81-,82-,83+,84+,85-,86-,87-/m1/s1
InChIKey	VYWNMRSGMCFFEF-OLKYIRNWSA-N

Species of Metabolite	Component	Source	Comments
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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150017) 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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150017) 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-Glc-(1→6)-β-D-Glc-(1→6)-β-D-Glc-yl}-1,2-dimyristoyl-sn-glycerol (CHEBI:150017) 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→6)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl}-1,2-bis(tetradecanoyloxy)-sn-glycerol

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→6)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl}-1,2-bis(tetradecanoyloxy)-sn-glycerol

Synonyms	Source
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-Glcp-(1→6)-β-D-Glcp-(1→6)-β-D-Glcp-yl}-1,2-dimyristoyl-sn-glycerol	ChEBI
(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-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-({[{[(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 acid	IUPAC
WH236	ChEBI

Citations