Showing metabocard for LPS with O-antigen (BMDB0063660)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-02-10 19:45:17 UTC
Update Date2020-04-22 15:54:34 UTC
BMDB IDBMDB0063660
Secondary Accession Numbers
  • BMDB63660
Metabolite Identification
Common NameLPS with O-antigen
DescriptionLPS with O-antigen, also known as endotoxin or lipopolysaccharide, 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. LPS with O-antigen is an extremely strong acidic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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
Polarizability521.6 ųChemAxon
Number of Rings18ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-3290000014-5b598407e93fb55bf094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-3680100109-186d0a18d234b570c2cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3950000000-821494a5093cc979f8d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1590000003-131cd3d40a4d833f88ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-3890000102-c4d4e0ded026f95dd34aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5890000010-beaaa06da4b2613e5b1bView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0013470
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available