CHEBI:84084 - 3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A)
ChEBI ID CHEBI:84084
ChEBI ASCII Name 3-PEA-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo-(2->6)-(de-O-acylated lipid A)
Definition A lipid A derivative that consists of a linear trisaccharide phosphate comprising an L-glycero-α-D-manno-heptose residue phosphoethanolamine-substituted on O-3, another L-glycero-α-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→3), (1→5) sequence, with the 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 icsA mutant of the core oligosaccharide of Neisseria meningitidis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C120H227N4O53P5
Net Charge 0
Average Mass 2728.95020
Monoisotopic Mass 2727.38786
InChI InChI=1S/C120H227N4O53P5/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(137)163-86(66-60-54-48-42-35-29-23-17-11-5)76-98(139)167-112-100(124-94(135)75-85(65-59-53-47-41-34-28-22-16-10-4)162-95(136)67-61-55-49-43-36-30-24-18-12-6)115(158-81-91-101(140)111(166-97(138)74-84(129)64-58-52-46-40-33-27-21-15-9-3)99(116(164-91)175-182(156,157)177-180(152,153)161-72-70-122)123-93(134)73-83(128)63-57-51-45-39-32-26-20-14-8-2)165-92(110(112)173-181(154,155)176-178(147,148)149)82-159-120(119(145)146)77-87(130)108(109(172-120)90(133)80-127)170-117-104(143)113(102(141)106(168-117)88(131)78-125)171-118-105(144)114(174-179(150,151)160-71-69-121)103(142)107(169-118)89(132)79-126/h83-92,99-118,125-133,140-144H,7-82,121-122H2,1-6H3,(H,123,134)(H,124,135)(H,145,146)(H,150,151)(H,152,153)(H,154,155)(H,156,157)(H2,147,148,149)/t83-,84-,85-,86-,87-,88+,89+,90-,91-,92-,99-,100-,101-,102-,103-,104+,105+,106-,107-,108-,109-,110-,111-,112-,113+,114+,115-,116-,117-,118-,120-/m1/s1
InChIKey XKWRWDCQEFNULL-CFDCENMDSA-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]3O)[C@H](O2)[C@H](O)CO)C(O)=O)[C@H]1OP(O)(=O)OP(O)(O)=O
ChEBI Ontology
Outgoing 3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a dodecanoate ester (CHEBI:87659)
3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a lipid As (CHEBI:25051)
3-PEA-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) (CHEBI:84084) is a tetradecanoate ester (CHEBI:87691)
IUPAC Name
(5R)-3-O-[(2-aminoethoxy)(hydroxy)phosphoryl]-5-[(1S)-1,2-dihydroxyethyl]-α-D-lyxopyranosyl-(1→3)-(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
3-PEA-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-α-Kdo-(2→6)-(de-O-acylated lipid A) ChEBI
Citation Waiting for Citations Type Source
24013955 PubMed citation Europe PMC
Last Modified
03 September 2015