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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:alpha-D-GlcpNAc-(1->2)-3-PEA-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A)
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Accession:CHEBI:84082 term browser browse the term
Definition:A lipid A derivative that consists of a linear tetrasaccharide phosphate comprising an N-acetyl-alpha-D-glucosamine residue,an L-glycero-alpha-D-manno-heptose residue phosphoethanolamine-substituted on O-3, another L-glycero-alpha-D-manno-heptose residue and a 3-deoxy-D-manno-oct-2-ulosonic acid (2-keto-3-deoxy-D-mannooctanoic acid, Kdo) in a (1->2), (1->3), (1->5) sequence, with the Kdo residue at the reducing end connected via an alpha(2->6) linkage to a de-O-acylated lipid A. Corresponds to the de-O-acylated lipid A conjugate of the icsB mutant of the core oligosaccharide of Neisseria meningitidis.
Synonyms:exact_synonym: 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1->2)-(5R)-3-O-[(2-aminoethoxy)(hydroxy)phosphoryl]-5-[(1S)-1,2-dihydroxyethyl]-alpha-D-lyxopyranosyl-(1->3)-(5R)-5-[(1S)-1,2-dihydroxyethyl]-alpha-D-lyxopyranosyl-(1->5)-(6R)-3-deoxy-6-[(1R)-1,2-dihydroxyethyl]-beta-L-erythro-hex-2-ulopyranonosyl-(2->)-2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-[hydroxy(phosphonooxy)phosphoryl]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-beta-D-glucopyranosyl-(1->6)-1-O-[{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-alpha-D-glucopyranose
 related_synonym: Formula=C128H240N5O58P5;   InChI=1S/C128H240N5O58P5/c1-8-14-20-26-32-38-39-45-51-57-63-69-100(148)175-89(67-61-55-49-43-36-30-24-18-12-5)77-102(150)180-118-105(133-98(146)76-88(66-60-54-48-42-35-29-23-17-11-4)174-99(147)68-62-56-50-44-37-31-25-19-13-6)122(170-83-95-107(152)117(179-101(149)75-87(140)65-59-53-47-41-34-28-22-16-10-3)104(124(177-95)189-196(168,169)191-194(164,165)173-73-71-130)132-97(145)74-86(139)64-58-52-46-40-33-27-21-15-9-2)178-96(116(118)187-195(166,167)190-192(159,160)161)84-171-128(127(157)158)78-90(141)114(115(186-128)93(144)81-136)183-125-111(156)119(109(154)112(181-125)91(142)79-134)184-126-121(185-123-103(131-85(7)138)108(153)106(151)94(82-137)176-123)120(188-193(162,163)172-72-70-129)110(155)113(182-126)92(143)80-135/h86-96,103-126,134-137,139-144,151-156H,8-84,129-130H2,1-7H3,(H,131,138)(H,132,145)(H,133,146)(H,157,158)(H,162,163)(H,164,165)(H,166,167)(H,168,169)(H2,159,160,161)/t86-,87-,88-,89-,90-,91+,92+,93-,94-,95-,96-,103-,104-,105-,106-,107-,108-,109-,110-,111+,112-,113-,114-,115-,116-,117-,118-,119+,120+,121+,122-,123-,124-,125-,126-,128-/m1/s1;   InChIKey=HGWNVQHQMSOYHF-GSKFDPOASA-N;   SMILES=CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](OP(O)(=O)OP(O)(=O)OCCN)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO[C@@]2(C[C@@H](O)[C@@H](O[C@H]3O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](OP(O)(=O)OCCN)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4NC(C)=O)[C@@H]3O)[C@H](O2)[C@H](O)CO)C(O)=O)[C@H]1OP(O)(=O)OP(O)(O)=O;   alpha-D-GlcNAc-(1->2)-3-PEA-L-alpha-D-Hep-(1->3)-L-alpha-D-Hep-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A)
 xref: PMID:24013955

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  CHEBI ontology 0
    role 0
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        antimicrobial agent 0
          antibacterial agent 0
            dodecanoic acid 0
              dodecanoate ester 0
                alpha-D-GlcpNAc-(1->2)-3-PEA-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A) 0
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                                                    alpha-D-GlcpNAc-(1->2)-3-PEA-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A) 0
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