lipid x
Description
lipid X: monosaccharide precursor of E coli lipid A; structure given in first source; see also lipid A precursors, Salmonella [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
lipid X : An N-acyl-D-glucosamine 1-phosphate where the N-acyl group is (R)-3-hydroxytetradecanoyl and carrying an additional (R)-3-hydroxytetradecanoyl group at the 3-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 123907 |
| CHEBI ID | 16942 |
| SCHEMBL ID | 10352307 |
| MeSH ID | M0129478 |
Synonyms (22)
| Synonym |
|---|
| 2-deoxy-3-o-[(3r)-3-hydroxytetradecanoyl]-2-{[(3r)-3-hydroxytetradecanoyl]amino}-1-o-phosphono-alpha-d-glucopyranose |
| 86559-73-1 |
| CHEBI:16942 |
| 2,3-bis[(3r)-3-hydroxymyristoyl]-alpha-d-glucosaminyl 1-phosphate |
| 2,3-diacylglucosamine 1-phosphate |
| C04824 |
| 2,3-bis(3-hydroxytetradecanoyl)-alpha-d-glucosaminyl 1-phosphate |
| lipid x |
| lp5 , |
| (r)-((2r,3s,4r,5r,6r)-3-hydroxy-2-(hydroxymethyl)-5-((r)-3-hydroxytetradecanamido)-6-(phosphonooxy)tetrahydro-2h-pyran-4-yl) 3-hydroxytetradecanoate |
| monosaccharide precursor, e coli lipid a |
| [(2r,3s,4r,5r,6r)-3-hydroxy-2-(hydroxymethyl)-5-[[(3r)-3-hydroxytetradecanoyl]amino]-6-phosphonooxyoxan-4-yl] (3r)-3-hydroxytetradecanoate |
| alpha-d-glucopyranose, 2-deoxy-2-((3-hydroxy-1-oxotetradecyl)amino)-, 1-(dihydrogen phosphate) 3-(3-hydroxytetradecanoate), (2(r),3(r))- |
| SCHEMBL10352307 |
| VJ1 , |
| Q27102143 |
| [(2r,3s,4r,5r,6r)-3-hydroxy-2-(hydroxymethyl)-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate |
| {[(2r,3r,4r,5s,6r)-5-hydroxy-6-(hydroxymethyl)-3- [(3r)-3-hydroxytetradecanamido]-4-{[(3r)-3- hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid |
| DTXSID901006919 |
| HY-130581 |
| CS-0109243 |
| AKOS040752595 |
Research Excerpts
Overview
Lipid X is a potential prototype compound for a new type of chemotherapy directed at blocking the harmful effects of LPS during bacterial septicemia. Lipid Y has the same structure as X, except for the additional presence of a palmitoyl moiety on the N-linked beta-hydroxymyristate.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Lipid X is a diacylglucosamine 1-phosphate bearing beta-hydroxymyristoyl groups at positions 2 and 3." | ( Enhancement of O2- generation and tumoricidal activity of murine macrophages by a monosaccharide precursor of Escherichia coli lipid A. Akagawa, K; Akamatsu, Y; Amano, F; Nishijima, M, 1985) | 0.99 |
| "Lipid X is a novel agent that enhances survival in an animal model of severe infection with gram-negative organisms." | ( Lipid X protects mice against fatal Escherichia coli infection. Craig, WA; Golenbock, DT; Leggett, JE; Proctor, RA; Raetz, CR; Rasmussen, P, 1988) | 2.44 |
| "Lipid X is a potential prototype compound for a new type of chemotherapy directed at blocking the harmful effects of LPS during bacterial septicemia." | ( Lipid X ameliorates pulmonary hypertension and protects sheep from death due to endotoxin. Golenbock, DT; Proctor, RA; Raetz, CR; Will, JA, 1987) | 2.44 |
| "Lipid X is a diacylglucosamine 1-phosphate bearing beta-hydroxymyristoyl groups at positions 2 and 3, and lipid Y has the same structure as X, except for the additional presence of a palmitoyl moiety on the N-linked beta-hydroxymyristate." | ( Macrophage activation by monosaccharide precursors of Escherichia coli lipid A. Akagawa, K; Akamatsu, Y; Amano, F; Nishijima, M; Raetz, CR; Tokunaga, T, 1985) | 0.99 |
Actions
| Excerpt | Reference | Relevance |
|---|---|---|
| "Lipid X was found to inhibit LPS-induced priming by directly interacting with the neutrophil in contrast to polymyxin B, which neutralized LPS by binding to it." | ( Inhibition of endotoxin-induced priming of human neutrophils by lipid X and 3-Aza-lipid X. Danner, RL; Joiner, KA; Parrillo, JE, 1987) | 1.23 |
Treatment
| Excerpt | Reference | Relevance |
|---|---|---|
| "Treatment with lipid X and ticarcillin over a broad range of antibiotic dosages in 362 mice demonstrated improved survival of two- to fourfold (P less than 0.0001 at 24 h after inoculation, P less than or equal to 0.0005 at 48 h, and P less than or equal to 0.0001 at 5 days)." | ( Lipid X protects mice against fatal Escherichia coli infection. Craig, WA; Golenbock, DT; Leggett, JE; Proctor, RA; Raetz, CR; Rasmussen, P, 1988) | 2.06 |
Dosage Studied
The pharmacokinetic profile of lipid X was investigated in sheep and in two strains of mice by using 32P-labeled lipid X. Dose-response studies revealed that lipid X induced the production of smaller amounts of the tumor-cytotoxic factor than LPS at low concentrations. It induced that of considerable amounts at and over 1 microgram/ml.
| Excerpt | Relevance | Reference |
|---|---|---|
| " Dose-response studies revealed that lipid X induced the production of smaller amounts of the tumor-cytotoxic factor than LPS at low concentrations, but it induced that of considerable amounts at and over 1 microgram/ml." | ( A monosaccharide precursor of Escherichia coli lipid A has the ability to induce tumor-cytotoxic factor production by a murine macrophage-like cell line, J774.1. Akamatsu, Y; Amano, F; Nishijima, M, 1986) | 0.54 |
Roles (1)
| Role | Description |
|---|---|
| Escherichia coli metabolite | Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Drug Classes (1)
| Class | Description |
|---|---|
| N-acyl-D-glucosamine 1-phosphate | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Pathways (1)
| Pathway | Proteins | Compounds |
|---|---|---|
| Lipid-A-precursor biosynthesis | 3 | 13 |
Research
Studies (67)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 34 (50.75) | 18.7374 |
| 1990's | 24 (35.82) | 18.2507 |
| 2000's | 3 (4.48) | 29.6817 |
| 2010's | 6 (8.96) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 23.60
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (23.60) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (2.99%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 65 (97.01%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||