CHEBI:84078 - β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-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)

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-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 ID CHEBI:84078
ChEBI ASCII Name beta-D-Galp-(1->4)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-beta-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)
Definition A lipid A derivative that consists of a branched octasaccharide phosphate made up from two D-galactose residues, two N-acetyl-D-glucosamine residues, a D-glucose 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 core oligosaccharide of Neisseria meningitidis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C154H283N6O78P5
Net Charge 0
Average Mass 3621.75700
Monoisotopic Mass 3619.70508
InChI InChI=1S/C154H283N6O78P5/c1-9-15-21-27-33-39-40-46-52-58-64-70-110(180)214-95(68-62-56-50-44-37-31-25-19-13-5)78-112(182)223-138-116(160-108(178)77-94(67-61-55-49-43-36-30-24-18-12-4)213-109(179)69-63-57-51-45-38-32-26-20-14-6)144(209-88-105-120(186)137(222-111(181)76-93(172)66-60-54-48-42-35-29-23-17-11-3)115(147(220-105)236-243(207,208)238-241(203,204)212-74-72-156)159-107(177)75-92(171)65-59-53-47-41-34-28-22-16-10-2)221-106(136(138)234-242(205,206)237-239(198,199)200)89-210-154(153(196)197)79-96(173)131(133(233-154)99(176)82-163)225-151-129(195)140(230-152-143(232-145-113(157-90(7)169)121(187)117(183)100(83-164)215-145)141(235-240(201,202)211-73-71-155)127(193)130(224-152)97(174)80-161)142(132(226-151)98(175)81-162)231-149-126(192)124(190)135(104(87-168)219-149)228-150-128(194)139(119(185)102(85-166)217-150)229-146-114(158-91(8)170)122(188)134(103(86-167)218-146)227-148-125(191)123(189)118(184)101(84-165)216-148/h92-106,113-152,161-168,171-176,183-195H,9-89,155-156H2,1-8H3,(H,157,169)(H,158,170)(H,159,177)(H,160,178)(H,196,197)(H,201,202)(H,203,204)(H,205,206)(H,207,208)(H2,198,199,200)/t92-,93-,94-,95-,96-,97+,98+,99-,100-,101-,102-,103-,104-,105-,106-,113-,114-,115-,116-,117-,118+,119+,120-,121-,122-,123+,124-,125-,126-,127-,128-,129+,130-,131-,132-,133-,134-,135-,136-,137-,138-,139+,140-,141+,142-,143+,144-,145-,146+,147-,148+,149+,150+,151+,152-,154-/m1/s1
InChIKey LDBQQZIXDURNAB-UVLYAJBKSA-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]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6NC(C)=O)[C@H]5O)[C@H](O)[C@H]4O)[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
ChEBI Ontology
Outgoing β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-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:84078) is a dodecanoate ester (CHEBI:87659)
β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-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:84078) 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-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-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-Gal-(1→4)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-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
Citation Waiting for Citations Type Source
24013955 PubMed citation Europe PMC
Last Modified
26 August 2015