P. gingivalis Kdo2-lipid A (penta-acylated, non-phosphorylated) (BioCAD00000769279)

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Metabolite Card

Formula: C109H198N2O32 (2047.3927)
SMILES: CCCCCCCCCCCCCCCC(O[C@H](CCCCCCCCCCCC(C)C)CC(N[C@H]3([C@@H](O[C@H](CO[C@@]2(C(=O)[O-])(O[C@H]([C@H](O)CO)[C@H](O)[C@H](O[C@]1(O[C@H]([C@@H](CO)O)[C@H](O)[C@H](O)C1)C(=O)[O-])C2))[C@H]([C@@H]3OC(C[C@H](O)CCCCCCCCCC(C)C)=O)O)OC[C@@H]4([C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCCC(C)C)[C@@H](O)O4)))=O)=O

Synonyms [en]

P. gingivalis Kdo2-lipid A (penta-acylated, 1,4'-bisdephosphorylated); P. gingivalis Kdo2-lipid A (penta-acylated, non-phosphorylated)

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

P. gingivalis Kdo2-lipid A (penta-acylated, non-phosphorylated). 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000769279). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

General BackgroundLipid A is a lipid component of the |FRAME: Lipopolysaccharides "lipopolysaccharides"| of Gram-negative bacteria. Its hydrophobic nature allows it to anchor the LPS to the outer membrane.Lipid A consists of two glucosamine units decorated with four to six acyl chains and one or two phosphate groups. Four β hydroxy acyl chains, 10 to 18 carbons in length, are attached directly to the glucosamine sugars at positions N-2 and O-3 (and N'-2 and O'-3, respectively), while two additional acyl chains are often attached to the β hydroxy group of two of the four β hydroxy acyl chains. The phosphate groups are attached at position O-1, O'-4, or both.Lipid A in |FRAME: TAX-837|While some bacteria have a highly conserved lipid A structure, the intracellular pathogen |FRAME: TAX-837| produces a highly variable lipid A. The different lipid A isoforms can exert opposite effects on the activation of the human Toll-like receptors TLR2 and TLR4, enabling the organism to orchestrate its virulence to control the host's innate immune pathway activation and biofilm dysbiosis |CITS: [19552698][29503705]|.The initial structure synthesized by |FRAME: TAX-837| is that of a |FRAME: CPD-24240 "penta-acylated and bisphosphorylated lipid A"|. The compound contains the methyl-branched fatty acids |FRAME: CPD-24244| and |FRAME: CPD-24271| (2 copies) as well as |FRAME: CPD-24242| and |FRAME: PALMITATE|, and there exists some variability in the composition and location of the acyl chains |CITS: [8405442][7721702]|. However, much greater variability is achieved by the combined action of several lipid A-modifying enzymes (|FRAME: EC-3.1.3.M10|, |FRAME: EC-3.1.3.M11|, and |FRAME: EC-3.1.1.77 "EC 3.1.1.77, lipid A deacylase"|) that produce a number of alternative forms, including tetra-acylated, non-phosphorylated structures that are inert for TLR2/TLR4 activation |CITS: [17335558][19552698]|.The different forms are often referred to by their molecular weights. However, note that the molecular weight describe the lipid A form without the |FRAME: KDO| (Kdo) acid sugar residues (a form that does not exist in nature).Forms observed in the organism include:Penta-acylated forms:
|FRAME: CPD-24240| (1768) |CITS: [7721702][16611234][16861633][19552698]|
|FRAME: CPD-24245| (1688) |CITS: [7721702][16611234][16861633][19552698]|
|FRAME: CPD-24256| (1688) |CITS: [19552698]|
|FRAME: CPD-24269| |CITS: [18263730][28320881]|Tetra-acylated (3'-deacylated) forms:
|FRAME: CPD-24243| (1449) |CITS: [16611234][16861633][19552698]|
|FRAME: CPD-24257| (1368) |CITS: [18263730][19552698]|Tetra-acylated (3-deacylated) forms:
|FRAME: CPD-24241| (1435) |CITS: [16861633][16611234]|Tri-acylated (3- and 3'-deacylated) forms:
|FRAME: CPD-24268| (1195) |CITS: [8405442][16861633]|

Entity Information

DBLinks

  • CAS Registry Number:
  • PubChem CID:
  • ChEBI:
  • HMDB:
  • LipidMaps:
  • KEGG:
  • BioCyc: CPD-24269
  • NCBI MeSH:
  • Wikipedia:
Other DBLinks
  • BioCyc: CPD-24269

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN-22272 3.1.3.- CPD-24256 + WATER --> CPD-24269 + Pi
BioCyc:RXN-22273 3.1.3.- CPD-24245 + WATER --> CPD-24269 + Pi
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Organism Source

Taxonomy Source

Pathway Synthetic

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