| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-08-29 05:56:41 UTC |
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| Update Date | 2016-11-09 01:09:04 UTC |
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| Accession Number | CHEM003194 |
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| Identification |
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| Common Name | Lipopolysaccharide |
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| Class | Small Molecule |
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| Description | Lipopolysaccharides (LPS), also known as lipoglycans and endotoxin, are large molecules consisting of a lipid and a polysaccharide composed of O-antigen, outer core and inner core joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria, and elicit strong immune responses in animals. LPS acts as the prototypical endotoxin because it binds the CD14/TLR4/MD2 receptor complex in many cell types, but especially in monocytes, dendritic cells, macrophages and B cells, which promotes the secretion of pro-inflammatory cytokines, nitric oxide, and eicosanoids. LPS is also an exogenous pyrogen (external fever-inducing substance). |
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| Contaminant Sources | |
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| Contaminant Type | - Amine
- Bacterial Toxin
- Ether
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C21H44NO9P |
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| Average Molecular Mass | 485.549 g/mol |
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| Monoisotopic Mass | 485.275 g/mol |
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| CAS Registry Number | Not Available |
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| IUPAC Name | (2S)-2-amino-3-({hydroxy[(2R)-2-hydroxy-3-{[(1R)-1-hydroxypentadecyl]oxy}propoxy]phosphoryl}oxy)propanoic acid |
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| Traditional Name | (2S)-2-amino-3-{[hydroxy(2R)-2-hydroxy-3-{[(1R)-1-hydroxypentadecyl]oxy}propoxyphosphoryl]oxy}propanoic acid |
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| SMILES | [H][C@@](O)(CO[C@@]([H])(O)CCCCCCCCCCCCCC)COP(O)(=O)OC[C@]([H])(N)C(O)=O |
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| InChI Identifier | InChI=1S/C21H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-20(24)29-15-18(23)16-30-32(27,28)31-17-19(22)21(25)26/h18-20,23-24H,2-17,22H2,1H3,(H,25,26)(H,27,28)/t18-,19+,20-/m1/s1 |
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| InChI Key | RPZLJDFLPRHXGM-HSALFYBXSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as glycerophosphoserines. These are lipids containing a glycerol moiety carrying a phosphoserine at the 3-position. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphoserines |
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| Direct Parent | Glycerophosphoserines |
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| Alternative Parents | |
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| Substituents | - Glycerophosphoserine
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Phosphoethanolamine
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Amino acid or derivatives
- Hemiacetal
- Amino acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic nitrogen compound
- Primary aliphatic amine
- Organic oxide
- Alcohol
- Carbonyl group
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Actin Cytoskeleton
- Actin Filament
- Apical Membrane
- Cell junction
- Cell surface
- Cytoplasm
- Cytoplasmic vesicle
- Cytoskeleton
- Early endosome
- Endoplasmic reticulum
- Endosome
- Extracellular
- Extracellular matrix
- Golgi apparatus
- Lysosome
- Microtubule
- Mitochondrion
- Nerve Fiber
- Nuclear Matrix
- Nuclear Membrane
- Nucleoplasm
- Plasma Membrane
- Ribosome
- Tubulin
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Apoptosis | Not Available | map04210 | | Lipopolysaccharide Biosynthesis | Not Available | Not Available | | Oxidative phosphorylation | Not Available | map00190 | | Osteoclast differentiation | Not Available | map04380 | | Salivary secretion | Not Available | map04970 | | Gastric acid secretion | Not Available | map04971 | | Endocytosis | Not Available | map04144 | | Renin-angiotensin system | Not Available | map04614 | | Proteasome | Not Available | Not Available | | Cell cycle | Not Available | map04110 | | Allograft Rejection | Not Available | Not Available | | Eicosanoids | Not Available | Not Available | | Cyclooxygenase Inhibitors | Not Available | Not Available | | Peptidoglycan Biosynthesis | Not Available | Not Available | | Notch signaling pathway | Not Available | map04330 | | Hedgehog Signaling Pathway | Not Available | Not Available | | Fatty acid Metabolism | SMP00051 | map00071 | | Abc transporters | Not Available | map02010 |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000l-9121500000-c9e2b4cc751b13619f6b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000f-9111000000-df7c9bbbadf8ec5286be | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000f-9410000000-6dab5d5f3b821deb1bdc | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0059-2293500000-380f1b38924608f1ef93 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9672100000-a141923d80411a945703 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-b2cdc16e81a9832299cc | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Lipopolysaccharides (LPS), also known as lipoglycans and endotoxin, are large molecules consisting of a lipid and a polysaccharide composed of O-antigen, outer core and inner core joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria, and elicit strong immune responses in animals. LPS acts as the prototypical endotoxin because it binds the CD14/TLR4/MD2 receptor complex in many cell types, but especially in monocytes, dendritic cells, macrophages and B cells, which promotes the secretion of pro-inflammatory cytokines, nitric oxide, and eicosanoids. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB04136 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | LPS |
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| Wikipedia Link | Not Available |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 17754066 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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