Record Information
Version1.0
Creation date2011-09-21 01:56:21 UTC
Update date2015-07-21 06:59:44 UTC
Primary IDFDB029471
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLPS core
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 LPS Core domain always contains an oligosaccharide component which attaches directly to lipid A and commonly contains sugars such as heptose and 3-deoxy-D-mannooctulosonic Acid (also known as KDO, keto-deoxyoctulosonate).[2] The LPS Cores of many bacteria also contain non-carbohydrate components, such as phosphate, amino acids, and ethanolamine substitutents.(from wiki) This card shows the LPS core component in E.coli. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Core oligosaccharideHMDB
Core oligosaccharide lipid aHMDB
Endotoxin lipopolysaccharide coreHMDB
Endotoxin LPS coreHMDB
Lipopolysaccharide core endotoxinHMDB
Lipopolysaccharide ra componentHMDB
Ra-LPSHMDB
core oligosaccharidehmdb
core oligosaccharide lipid Ahmdb
endotoxin Lipopolysaccharide corehmdb
endotoxin LPS corehmdb
Lipopolysaccharide core endotoxinhmdb
Lipopolysaccharide Ra componenthmdb
LPS corehmdb
Predicted Properties
PropertyValueSource
logP1.54ChemAxon
pKa (Strongest Acidic)0.4ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count91ChemAxon
Hydrogen Donor Count53ChemAxon
Polar Surface Area1673.8 ŲChemAxon
Rotatable Bond Count145ChemAxon
Refractivity963.45 m³·mol⁻¹ChemAxon
Number of Rings13ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC175H317N5O101P6
IUPAC name(2R,4R,5S,6R)-5-{[(3S,4R,5R,6R)-5-[({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4S,5R,6R)-6-[(1S)-2-{[(3S,4R,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonooxy)oxan-2-yl]oxy}-1-hydroxyethyl]-4-{[(3R,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3-{[(3R,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-hydroxyoxan-2-yl]oxy}-4-{[(2R,4R,5S,6R)-4-{[(2R,4R,5R,6R)-4-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy}-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C175H317N5O101P6/c1-8-14-20-26-32-38-39-45-51-57-63-69-118(202)252-98(67-61-55-49-43-36-30-24-18-12-5)77-120(204)261-152-123(180-116(200)76-97(66-60-54-48-42-35-29-23-17-11-4)251-117(201)68-62-56-50-44-37-31-25-19-13-6)160(246-91-112-130(211)151(260-119(203)75-96(192)65-59-53-47-41-34-28-22-16-10-3)122(162(257-112)280-284(236,237)238)179-115(199)74-95(191)64-58-52-46-40-33-27-21-15-9-2)259-114(150(152)277-282(230,231)232)93-248-173(170(224)225)80-107(272-174(171(226)227)78-105(128(209)144(273-174)99(193)81-181)271-175(172(228)229)79-106(276-285(239,240)249-72-70-176)129(210)145(274-175)100(194)82-182)149(148(275-173)103(197)85-185)265-167-142(223)155(159(147(264-167)102(196)84-184)279-287(243,244)281-286(241,242)250-73-71-177)268-166-141(222)154(139(220)143(262-166)104(198)90-245-164-138(219)136(217)156(278-283(233,234)235)146(263-164)101(195)83-183)266-165-140(221)153(131(212)113(258-165)92-247-163-137(218)133(214)125(206)109(87-187)254-163)267-168-158(135(216)127(208)110(88-188)255-168)270-169-157(134(215)126(207)111(89-189)256-169)269-161-121(178-94(7)190)132(213)124(205)108(86-186)253-161/h95-114,121-169,181-189,191-198,205-223H,8-93,176-177H2,1-7H3,(H,178,190)(H,179,199)(H,180,200)(H,224,225)(H,226,227)(H,228,229)(H,239,240)(H,241,242)(H,243,244)(H2,230,231,232)(H2,233,234,235)(H2,236,237,238)/t95-,96-,97-,98-,99+,100+,101+,102+,103+,104+,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,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-,153+,154+,155-,156+,157-,158-,159-,160-,161+,162-,163+,164?,165?,166?,167?,168-,169?,173-,174-,175-/m1/s1
InChI KeyAAXCQFOXUJMCCW-PETQGJDISA-N
Isomeric SMILESCCCCCCCCCCCCCC(=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)=O)[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@@]3(C[C@@H](O[C@@]4(C[C@@H](OP(O)(=O)OCCN)[C@H](O)[C@H](O4)[C@@H](O)CO)C(O)=O)[C@H](O)[C@H](O3)[C@@H](O)CO)C(O)=O)[C@H](OC3O[C@H]([C@@H](O)CO)[C@@H](OP(O)(=O)OP(O)(=O)OCCN)[C@H](OC4O[C@H]([C@@H](O)COC5O[C@H]([C@@H](O)CO)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H]5O)[C@@H](O)[C@H](OC5O[C@H](CO[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6OC6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6NC(C)=O)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@H](O2)[C@@H](O)CO)C(O)=O)[C@H]1OP(O)(O)=O
Average Molecular Weight4293.205
Monoisotopic Molecular Weight4290.824851063
Classification
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
  • Polysaccharide
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Organic pyrophosphate
  • Phosphoethanolamine
  • Beta-hydroxy acid
  • Ketal
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyran
  • Fatty amide
  • Hydroxy acid
  • N-acyl-amine
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Acetamide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Carboxamide group
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary alcohol
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3190100203-6cc73cac6ee8b6f34f63JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01zc-9271311813-15153f67fde929abb801JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9882221311-ce1866014f1c60c8f6d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-4091010001-e7a6007021379e3bde15JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9150000010-b9005aa390051477aed9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-68958ff65e8f5e748306JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC0338
Pubchem Compound ID53481794
Pubchem Substance IDNot Available
ChEBI ID59309
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13471
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLipopolysaccharide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference