LPS-o-antigen (CHEM041266)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:18:03 UTC
Update Date2016-11-09 01:22:26 UTC
Accession NumberCHEM041266
Identification
Common NameLPS-o-antigen
ClassSmall Molecule
DescriptionLipopolysaccharides (LPS), also known as lipoglycans, are large molecules consisting of a lipid and a polysaccharide joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria, act as endotoxins and elicit strong immune responses in animals. LPS is the major component of the outer membrane of Gram-negative bacteria, contributing greatly to the structural integrity of the bacteria, and protecting the membrane from certain kinds of chemical attack. LPS also increases the negative charge of the cell membrane and helps stabilize the overall membrane structure. It is of crucial importance to gram negative bacteria, whose death results if it is mutated or removed. LPS is an endotoxin, and induces a strong response from normal animal immune systems. LPS acts as the prototypical endotoxin because it binds the CD14/TLR4/MD2 receptor complex, which promotes the secretion of pro-inflammatory cytokines in many cell types, but especially in macrophages. In Immunology, the term "LPS challenge" refers to the process of exposing a subject to an LPS which may act as a toxin. LPS is also an exogenous pyrogen (external fever-inducing substance). Being of crucial importance to gram negative bacteria, these molecules make candidate targets for new antimicrobial agents. LPS comprises three parts: 1. O antigen (or O polysaccharide). 2. Core polysaccharide. 3. Lipid A The making of LPS can be modified in order to present a specific sugar structure. Those can be recognised by either other LPS (which enables to inhibit LPS toxins) or glycosyltransferases which use those sugar structure to add more specific sugars. It has recently been shown that a specific enzyme in the intestine (alkaline phosphatase) can detoxify LPS by removing the two phosphate groups found on LPS carbohydrates [6]. This may function as an adaptive mechanism to help the host manage potentially toxic effects of gram-negative bacteria normally found in the small intestine. (from wiki) This card shows the example of LPS in E. coli with one o-antigen unit. [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC93H175N2O21P
Average Molecular Mass1688.390 g/mol
Monoisotopic Mass1687.242 g/mol
CAS Registry NumberNot Available
IUPAC NameN-[2-({5-[(1,3-dihydroxytetradecylidene)amino]-6-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl}oxy)-6-(hydroxymethyl)-5-(phosphonooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]-3-(dodecanoyloxy)tetradecanimidic acid
Traditional NameN-[2-({5-[(1,3-dihydroxytetradecylidene)amino]-6-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl}oxy)-6-(hydroxymethyl)-5-(phosphonooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]-3-(dodecanoyloxy)tetradecanimidic acid
SMILESCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP(O)(O)=O)C(CO)OC(OC2CC(OC(=O)CC(O)CCCCCCCCCCC)C(N=C(O)CC(O)CCCCCCCCCCC)C(O)O2)C1N=C(O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
InChI IdentifierInChI=1S/C93H175N2O21P/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(102)110-78(66-60-54-48-42-35-29-23-17-11-5)72-86(104)113-91-89(95-82(100)71-77(65-59-53-47-41-34-28-22-16-10-4)109-83(101)67-61-55-49-43-36-30-24-18-12-6)93(112-80(74-96)90(91)116-117(106,107)108)115-87-73-79(111-85(103)70-76(98)64-58-52-46-40-33-27-21-15-9-3)88(92(105)114-87)94-81(99)69-75(97)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-93,96-98,105H,7-74H2,1-6H3,(H,94,99)(H,95,100)(H2,106,107,108)
InChI KeyHSNYRLYFFRIIEC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • Tetracarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • N-acyl-amine
  • Oxane
  • Carboxamide group
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00049 g/LALOGPS
logP7.28ALOGPS
logP25.58ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)0.52ChemAxon
pKa (Strongest Basic)4.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area345.75 ŲChemAxon
Rotatable Bond Count85ChemAxon
Refractivity460.91 m³·mol⁻¹ChemAxon
Polarizability206.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB029470
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID44268108
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available