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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-05-06 10:19:23 UTC
Update Date2020-02-26 21:38:41 UTC
HMDB IDHMDB0013470
Secondary Accession Numbers
  • HMDB13470
Metabolite Identification
Common NameLPS with O-antigen
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. LPS with O-antigen has been found to be a metabolite of Escherichia, Pseudomonas and Salmonella (PMID: 12045108 ).
Structure
Open uri20200226 28264 gedljk?1582753121
Synonyms
ValueSource
EndotoxinHMDB
Endotoxin lipopolysaccharideHMDB
Endotoxin LPSHMDB
LipopolysaccharideHMDB
Lipopolysaccharide with O-antigenHMDB
LPSHMDB
Chemical FormulaC211H376N8O126P6
Average Molecular Weight5227.0637
Monoisotopic Molecular Weight5224.168615516
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,5R,6R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3R,4R,5R,6R)-3-acetamido-6-({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxyoxan-2-yl]oxy}-5-hydroxy-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
Traditional 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,5R,6R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3R,4R,5R,6R)-3-acetamido-6-({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxyoxan-2-yl]oxy}-5-hydroxy-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
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=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]7O[C@H](CO[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8NC(C)=O)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@H](O)[C@H](O[C@H]9O[C@H](CO[C@H]%10O[C@H](CO)[C@H](O)[C@H](O)[C@H]%10O)[C@H](O)[C@H](O)[C@H]9O)[C@H]8NC(C)=O)[C@H]7NC(C)=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
InChI Identifier
InChI=1S/C211H376N8O126P6/c1-11-17-23-29-35-41-42-48-54-60-66-72-134(247)308-109(70-64-58-52-46-39-33-27-21-15-5)80-136(249)322-182-142(219-132(245)79-108(69-63-57-51-45-38-32-26-20-14-4)307-133(246)71-65-59-53-47-40-34-28-22-16-6)192(301-99-128-153(260)179(321-135(248)78-107(237)68-62-56-50-44-37-31-25-19-13-3)141(196(317-128)344-348(290,291)292)218-131(244)77-106(236)67-61-55-49-43-36-30-24-18-12-2)320-130(178(182)341-346(284,285)286)101-304-209(206(278)279)83-118(336-210(207(280)281)81-116(149(256)172(337-210)110(238)84-220)335-211(208(282)283)82-117(340-349(293,294)305-75-73-212)150(257)173(338-211)111(239)85-221)177(176(339-209)114(242)88-224)326-203-170(277)186(189(175(325-203)113(241)87-223)343-351(297,298)345-350(295,296)306-76-74-213)332-202-169(276)184(167(274)171(323-202)115(243)96-299-199-166(273)162(269)187(342-347(287,288)289)174(324-199)112(240)86-222)329-201-168(275)183(155(262)129(319-201)100-303-198-164(271)159(266)146(253)122(92-228)313-198)330-204-188(161(268)147(254)123(93-229)314-204)333-205-190(334-193-138(215-103(8)233)157(264)144(251)120(90-226)310-193)185(152(259)125(95-231)315-205)331-195-140(217-105(10)235)181(154(261)127(316-195)98-300-191-137(214-102(7)232)156(263)143(250)119(89-225)309-191)327-194-139(216-104(9)234)180(151(258)124(94-230)311-194)328-200-165(272)160(267)148(255)126(318-200)97-302-197-163(270)158(265)145(252)121(91-227)312-197/h106-130,137-205,220-231,236-243,250-277H,11-101,212-213H2,1-10H3,(H,214,232)(H,215,233)(H,216,234)(H,217,235)(H,218,244)(H,219,245)(H,278,279)(H,280,281)(H,282,283)(H,293,294)(H,295,296)(H,297,298)(H2,284,285,286)(H2,287,288,289)(H2,290,291,292)/t106-,107-,108-,109-,110+,111+,112+,113+,114+,115+,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,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+,170+,171-,172-,173-,174-,175-,176-,177+,178-,179-,180-,181-,182-,183+,184+,185+,186-,187+,188-,189-,190-,191-,192-,193+,194+,195+,196-,197+,198+,199?,200-,201?,202?,203?,204-,205?,209-,210-,211-/m1/s1
InChI KeyBFVQTKQTUCQRPI-YYEZTRBPSA-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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-8.2ChemAxon
pKa (Strongest Acidic)0.4ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count116ChemAxon
Hydrogen Donor Count68ChemAxon
Polar Surface Area2096.16 ŲChemAxon
Rotatable Bond Count163ChemAxon
Refractivity1158.82 m³·mol⁻¹ChemAxon
Number of Rings18ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000014 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0000027 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0000096 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00338
BioCyc IDCPD0-2294
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481793
PDB IDNot Available
ChEBI ID16412
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Raetz CR, Whitfield C: Lipopolysaccharide endotoxins. Annu Rev Biochem. 2002;71:635-700. doi: 10.1146/annurev.biochem.71.110601.135414. Epub 2001 Nov 9. [PubMed:12045108 ]