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CHEBI:84081 - β-D-Glcp-(1→4)-[α-D-GlcpNAc-(1→2)-3-PEA-L-α-D-Hepp-(1→3)]-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)

ChEBI IDCHEBI:84081
ChEBI Nameβ-D-Glcp-(1→4)-[α-D-GlcpNAc-(1→2)-3-PEA-L-α-D-Hepp-(1→3)]-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)
Stars
ASCII Namebeta-D-Glcp-(1->4)-[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)
DefinitionA lipid A derivative that consists of a branched pentasaccharide phosphate made up from a D-glucose residue, an N-acetyl-D-glucosamine residue, two L-glycero-D-manno-heptose residues (one of which is phosphoethanolamine-substituted on O-3), with linkages as shown and with a 3-deoxy-D-manno-oct-2-ulosonic acid (2-keto-3-deoxy-D-mannooctanoic acid, Kdo) residue at the reducing end connected via an α(2→6) linkage to a de-O-acylated lipid A. Corresponds to the de-O-acylated lipid A conjugate of the galE mutant of the core oligosaccharide of Neisseria meningitidis.
Last Modified26 August 2015
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC134H250N5O63P5
Net Charge0
Average Mass3094.316
Monoisotopic Mass3092.52006
SMILES[H][C@]1([C@H](O)CO)O[C@@](OC[C@H]2O[C@@H](OC[C@H]3O[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]3O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H]2OP(=O)(O)OP(=O)(O)O)(C(=O)O)C[C@@H](O)[C@H]1O[C@H]1O[C@]([H])([C@@H](O)CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O[C@H]2O[C@]([H])([C@@H](O)CO)[C@@H](O)[C@H](OP(=O)(O)OCCN)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O
InChIInChI=1S/C134H250N5O63P5/c1-8-14-20-26-32-38-39-45-51-57-63-69-102(155)184-90(67-61-55-49-43-36-30-24-18-12-5)77-104(157)190-122-107(139-100(153)76-89(66-60-54-48-42-35-29-23-17-11-4)183-101(154)68-62-56-50-44-37-31-25-19-13-6)127(179-84-97-110(160)121(189-103(156)75-88(147)65-59-53-47-41-34-28-22-16-10-3)106(129(187-97)200-207(177,178)202-205(173,174)182-73-71-136)138-99(152)74-87(146)64-58-52-46-40-33-27-21-15-9-2)188-98(120(122)198-206(175,176)201-203(168,169)170)85-180-134(133(166)167)78-91(148)117(119(197-134)94(151)81-142)192-131-115(165)123(125(118(193-131)93(150)80-141)195-130-113(163)112(162)109(159)96(83-144)186-130)194-132-126(196-128-105(137-86(7)145)111(161)108(158)95(82-143)185-128)124(199-204(171,172)181-72-70-135)114(164)116(191-132)92(149)79-140/h87-98,105-132,140-144,146-151,158-165H,8-85,135-136H2,1-7H3,(H,137,145)(H,138,152)(H,139,153)(H,166,167)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H2,168,169,170)/t87-,88-,89-,90-,91-,92+,93+,94-,95-,96-,97-,98-,105-,106-,107-,108-,109-,110-,111-,112+,113-,114-,115+,116-,117-,118-,119-,120-,121-,122-,123-,124+,125-,126+,127-,128-,129-,130+,131+,132-,134-/m1/s1
InChIKeyOUNZLQARUOSTJA-FREUHNCJSA-N
ChEBI Ontology
Outgoing Relation(s)
β-D-Glcp-(1→4)-[α-D-GlcpNAc-(1→2)-3-PEA-L-α-D-Hepp-(1→3)]-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84081) is a dodecanoate ester (CHEBI:87659)
β-D-Glcp-(1→4)-[α-D-GlcpNAc-(1→2)-3-PEA-L-α-D-Hepp-(1→3)]-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84081) is a lipid As (CHEBI:25051)
IUPAC Name 
2-acetamido-2-deoxy-α-D-glucopyranosyl-(1→2)-(5R)-3-O-[(2-aminoethoxy)(hydroxy)phosphoryl]-5-[(1S)-1,2-dihydroxyethyl]-α-D-lyxopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-(5R)-5-[(1S)-1,2-dihydroxyethyl]-α-D-lyxopyranosyl-(1→5)-(6R)-3-deoxy-6-[(1R)-1,2-dihydroxyethyl]-β-L-erythro-hex-2-ulopyranonosyl-(2→6)-2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-[hydroxy(phosphonooxy)phosphoryl]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-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}-α-D-glucopyranose
Synonym  Source
β-D-Glc-(1→4)-[α-D-GlcNAc-(1→2)-3-PEA-L-α-D-Hep-(1→3)]-L-α-D-Hep-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)ChEBI
Citations