CHEBI ONTOLOGY - ANNOTATIONS
The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/ . The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/ ). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term: lipopolysaccharide
Accession: CHEBI:16412
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Definition: Liposaccharide natural compounds consisting of a trisaccharide repeating unit (two heptose units and octulosonic acid) with oligosaccharide side chains and 3-hydroxytetradecanoic acid units (they are a major constituent of the cell walls of Gram-negative bacteria).
Synonyms: related_synonym: LPS; lipopolysaccharides
alt_id: CHEBI:14520; CHEBI:25062; CHEBI:6494; MESH:D008070
xref: KEGG:C00338
xref_mesh: MESH:D008070
xref: PMID:15589368; PMID:24186868; PMID:24506665; PMID:24642373; PMID:24659348
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Path 1
CHEBI ontology
19831
chemical entity
19829
molecular entity
19829
polyatomic entity
19787
macromolecule
8787
biomacromolecule
8327
polysaccharide derivative
5116
lipopolysaccharide
4083
(1R,2S,4R,5R,8R,9S,11S)-9-ormyl-2-[[(2R,3S,4S,5R,6R)-3-hydroxy-6-(hydroxymethyl)-5-methoxy-4-[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxyoxan-2-yl]oxymethyl]-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
0
(Z)-2,6-dimethyl-7-(4-methyl-5-oxooxolan-2-yl)-3-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]hept-5-enoic acid
0
1-O-alpha-D-glucopyranosyl-(2-hexadecanoyloxy)-eicosan-1-ol
0
10-Hydroxy-octadec-12Z-enoate-9-beta-D-glucuronide
0
1050-Da MAA
0
11,13-Dihydrotaraxinic acid glucosyl ester
0
12-Hydroxy-13-O-D-glucuronoside-octadec-9Z-enoate
0
12-O-D-Glucuronoside-13-hydroxyoctadec-9Z-enoate
0
14-O-(alpha-D-glucopyranosyl)-7S,14S-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
14-O-(alpha-D-mannopyranosyl)-7S,14S-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
14-O-(beta-D-glucopyranosyl)-7S,14R-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
19-Hydroxydeacetylnomilinic acid 17-beta-D-glucopyranoside
0
2,3-di-0-hexanoyl-alpha-glucopyranose
0
2-Phenylethyl 3-O-(4-carboxy-3-hydroxy-3-methylbutanoyl)-beta-D-glucopyranoside
0
2-methylidene-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanoic acid
0
3,4,5-trihydroxy-6-\{[5-(4-methoxyphenyl)-2-methyl-3-oxopent-4-en-2-yl]oxy\}oxane-2-carboxylic acid
0
3,5-Dihydroxy-4-[3,4,5-trihydroxy-6-[[4-(2-hydroxypropan-2-yl)cyclohexene-1-carbonyl]oxymethyl]oxan-2-yl]oxybenzoic acid
0
3-deoxyoctulosonyllipopolysaccharide
0
4-O-alpha-Galactopyranuronosyl-galacturonic acid
0
5-[[4,5-dihydroxy-6-[(6E)-8-methoxy-3,7-dimethyl-8-oxoocta-1,6-dien-3-yl]oxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
0
6-(1-carboxypropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-(3-carboxypropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-O-(2-methylbutanoyl)-alpha-D-glucopyranosyl alpha-D-glucopyranoside
0
6-O-(3R,4-dihydroxy-2-methylene-butanoyl)-beta-D-glucopyranose
0
6-O-(4-hydroxy-2-methylene-butanoyl)-beta-D-glucopyranose
0
6-O-(6-O-pentadecanoyl-alpha-D-glucopyranosyl)-1-O-pentadecanoyl-alpha-D-glucopyranose
0
6-O-Oleuropeoylsucrose
0
6-[(1-carboxypropan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[(3-carboxy-2-methylprop-2-en-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[3-acetamido-2-[2-[5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-[[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl]-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid
0
6-[4-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[5-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-\{[6-(2-carboxyeth-1-en-1-yl)-4-methoxy-2H-1,3-benzodioxol-5-yl]oxy\}-3,4,5-trihydroxyoxane-2-carboxylic acid
0
9-Hydroxy-10-O-D-glucuronoside-12Z-octadecenoate
0
Acremomannolipin A
0
Actinotetraose I
0
Actinotetraose J
0
Actinotetraose K
0
Actinotetraose L
0
Actinotetraose hexatiglate
0
Ambofuracin
0
BE-29602
0
BU-4794F
0
Butyl 4'-O-butanoyl-6-O-hexadecanoyl-neohesperidoside
0
Cordyglycoside A
0
Corynecandin
0
Cosmosporaside D
0
Cosmosporaside D, (rel)-
0
Cosmosporaside E
0
Cosmosporaside E, (rel)-
0
Cycloviracin B2
0
E. coli strain 0111 B4 lipopolysaccharide
0
Emmyguyacin A
0
Emmyguyacin B
0
Eucaglobulin
0
F-10748 A1
0
F-10748 B1
0
F-10748 B2
0
F-10748 C1
0
F-10748 C2
0
F-10748 D1
0
F-10748 D2
0
Fattiviracin FV-10
0
Fattiviracin FV-4
0
Fattiviracin FV-8
0
Fattiviracin FV-9
0
Glucolipsin A
0
Glucolipsin B
0
Glucoselysine
0
Glucoselysine-6-phosphate
0
Glycosylated Palythine-threonine
0
Gobienine A
0
Gobienine C
0
HCH-acetylsalicortin
0
Iedoglucomide A
0
Ieodoglucomide C
0
Isolimonic acid glucoside
0
LSM-36656
0
LSM-36728
0
LSM-36730
0
LSM-36740
0
Mer-WF3010
0
N-acetyl-D-glucosaminyllipopolysaccharides
0
N-acetyl-beta-D-mannosaminouronosyl-(1->4)-lipopolysaccharide
0
N2-Maltulosylarginine
0
Nomilinic acid 17-glucoside
0
S. salinus M19-40T lipid A
0
S4:18(p3:16/f1:2)
0
Saricandin
0
Secaloside A
0
Specnuezhenide
0
Suomilide
0
Trehalose-6,6'-dicorynomycolate
0
Trehangelin A
0
Trehangelin B
0
Trehangelin C
0
Ustilagic acid
0
Ustilagic acid C
0
Ustilipid A
0
Ustilipid B
0
Ustilipid D1
0
Ustilipid D2
0
Ustilipid E1
0
Ustilipid E2
0
Ustilipid E3
0
Ustilipid F1
0
Ustilipid F2
0
Ustilipid F3
0
[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-5-[[(3R)-3-decanoyloxydodecanoyl]amino]-3,4-dihydroxy-6-phosphonooxyoxan-2-yl]methoxy]-3-[[(3R)-3-dodecanoyloxydodecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxyoxan-4-yl] (3R)-3-hydroxydodecanoate
0
[(2R,3S,4R,5R,6R)-5-[[(3R)-3-decanoyloxydodecanoyl]amino]-2-[[(2R,3R,4R,5S,6R)-3-[[(3R)-3-dodecanoyloxydodecanoyl]amino]-4-[(3R)-3-hydroxydodecanoyl]oxy-6-(hydroxymethyl)-5-phosphonooxyoxan-2-yl]oxymethyl]-3-hydroxy-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxydodecanoate
0
[(2R,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 7-methyloctanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 8-methylnonanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 9-methyldecanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]methyl 3,4-dihydroxy-2-methylidenebutanoate
0
[(2r,3r,4s,5s,6r)-3-acetyloxy-2-(acetyloxymethyl)-5-hexanoyloxy-6-[(2s,3r)-2,3,4-trihydroxybutoxy]oxan-4-yl] tetradecanoate
0
[2-[4-Hydroxy-2,5-bis(hydroxymethyl)-3-(3-methylbutanoyloxy)oxolan-2-yl]oxy-6-(hydroxymethyl)-4,5-bis(2-methylpropanoyloxy)oxan-3-yl] decanoate
0
[3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoate
0
[6-[[6-[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-2-methylbut-2-enoate
0
alpha,alpha'-Trehalose 4,6-dioleate
0
alpha,alpha'-Trehalose 6,6'-dipalmitate
0
alpha,alpha'-Trehalose 6-palmitate
0
beta-D-Fructofuranosyl 4-O-(2-methylbutanoyl)-alpha-D-glucopyranoside
0
beta-D-Fructofuranosyl 4-O-decanoyl-alpha-D-glucopyranoside
0
beta-D-Fructofuranosyl 4-O-dodecanoyl-alpha-D-glucopyranoside
0
citrusoside A
0
citrusoside B
0
citrusoside C
0
citrusoside D
0
galactosyllipopolysaccharide +
0
glucosyllipopolysaccharide +
0
soldanelline B
0
Path 2
CHEBI ontology
19831
subatomic particle
19829
composite particle
19829
hadron
19829
baryon
19829
nucleon
19829
atomic nucleus
19829
atom
19829
main group element atom
19779
p-block element atom
19779
carbon group element atom
19728
carbon atom
19724
organic molecular entity
19724
heteroorganic entity
19477
organochalcogen compound
19240
organooxygen compound
19155
carbohydrates and carbohydrate derivatives
15289
carbohydrate
15289
polysaccharide
8208
polysaccharide derivative
5116
O-polysaccharide
4083
lipopolysaccharide
4083
(1R,2S,4R,5R,8R,9S,11S)-9-ormyl-2-[[(2R,3S,4S,5R,6R)-3-hydroxy-6-(hydroxymethyl)-5-methoxy-4-[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxyoxan-2-yl]oxymethyl]-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
0
(Z)-2,6-dimethyl-7-(4-methyl-5-oxooxolan-2-yl)-3-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]hept-5-enoic acid
0
1-O-alpha-D-glucopyranosyl-(2-hexadecanoyloxy)-eicosan-1-ol
0
10-Hydroxy-octadec-12Z-enoate-9-beta-D-glucuronide
0
1050-Da MAA
0
11,13-Dihydrotaraxinic acid glucosyl ester
0
12-Hydroxy-13-O-D-glucuronoside-octadec-9Z-enoate
0
12-O-D-Glucuronoside-13-hydroxyoctadec-9Z-enoate
0
14-O-(alpha-D-glucopyranosyl)-7S,14S-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
14-O-(alpha-D-mannopyranosyl)-7S,14S-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
14-O-(beta-D-glucopyranosyl)-7S,14R-dihydroxy-7,9,13,17-tetramethyl-2E,4E,8E,10E,12E,16E-octadecahexaenoic acid
0
19-Hydroxydeacetylnomilinic acid 17-beta-D-glucopyranoside
0
2,3-di-0-hexanoyl-alpha-glucopyranose
0
2-Phenylethyl 3-O-(4-carboxy-3-hydroxy-3-methylbutanoyl)-beta-D-glucopyranoside
0
2-methylidene-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanoic acid
0
3,4,5-trihydroxy-6-\{[5-(4-methoxyphenyl)-2-methyl-3-oxopent-4-en-2-yl]oxy\}oxane-2-carboxylic acid
0
3,5-Dihydroxy-4-[3,4,5-trihydroxy-6-[[4-(2-hydroxypropan-2-yl)cyclohexene-1-carbonyl]oxymethyl]oxan-2-yl]oxybenzoic acid
0
3-deoxyoctulosonyllipopolysaccharide
0
4-O-alpha-Galactopyranuronosyl-galacturonic acid
0
5-[[4,5-dihydroxy-6-[(6E)-8-methoxy-3,7-dimethyl-8-oxoocta-1,6-dien-3-yl]oxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
0
6-(1-carboxypropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-(3-carboxypropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-O-(2-methylbutanoyl)-alpha-D-glucopyranosyl alpha-D-glucopyranoside
0
6-O-(3R,4-dihydroxy-2-methylene-butanoyl)-beta-D-glucopyranose
0
6-O-(4-hydroxy-2-methylene-butanoyl)-beta-D-glucopyranose
0
6-O-(6-O-pentadecanoyl-alpha-D-glucopyranosyl)-1-O-pentadecanoyl-alpha-D-glucopyranose
0
6-O-Oleuropeoylsucrose
0
6-[(1-carboxypropan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[(3-carboxy-2-methylprop-2-en-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[3-acetamido-2-[2-[5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-[[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl]-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid
0
6-[4-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-[5-(4-carboxy-2-hydroxybutyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
0
6-\{[6-(2-carboxyeth-1-en-1-yl)-4-methoxy-2H-1,3-benzodioxol-5-yl]oxy\}-3,4,5-trihydroxyoxane-2-carboxylic acid
0
9-Hydroxy-10-O-D-glucuronoside-12Z-octadecenoate
0
Acremomannolipin A
0
Actinotetraose I
0
Actinotetraose J
0
Actinotetraose K
0
Actinotetraose L
0
Actinotetraose hexatiglate
0
Ambofuracin
0
BE-29602
0
BU-4794F
0
Butyl 4'-O-butanoyl-6-O-hexadecanoyl-neohesperidoside
0
Cordyglycoside A
0
Corynecandin
0
Cosmosporaside D
0
Cosmosporaside D, (rel)-
0
Cosmosporaside E
0
Cosmosporaside E, (rel)-
0
Cycloviracin B2
0
E. coli strain 0111 B4 lipopolysaccharide
0
Emmyguyacin A
0
Emmyguyacin B
0
Eucaglobulin
0
F-10748 A1
0
F-10748 B1
0
F-10748 B2
0
F-10748 C1
0
F-10748 C2
0
F-10748 D1
0
F-10748 D2
0
Fattiviracin FV-10
0
Fattiviracin FV-4
0
Fattiviracin FV-8
0
Fattiviracin FV-9
0
Glucolipsin A
0
Glucolipsin B
0
Glucoselysine
0
Glucoselysine-6-phosphate
0
Glycosylated Palythine-threonine
0
Gobienine A
0
Gobienine C
0
HCH-acetylsalicortin
0
Iedoglucomide A
0
Ieodoglucomide C
0
Isolimonic acid glucoside
0
LSM-36656
0
LSM-36728
0
LSM-36730
0
LSM-36740
0
Mer-WF3010
0
N-acetyl-D-glucosaminyllipopolysaccharides
0
N-acetyl-beta-D-mannosaminouronosyl-(1->4)-lipopolysaccharide
0
N2-Maltulosylarginine
0
Nomilinic acid 17-glucoside
0
S. salinus M19-40T lipid A
0
S4:18(p3:16/f1:2)
0
Saricandin
0
Secaloside A
0
Specnuezhenide
0
Suomilide
0
Trehalose-6,6'-dicorynomycolate
0
Trehangelin A
0
Trehangelin B
0
Trehangelin C
0
Ustilagic acid
0
Ustilagic acid C
0
Ustilipid A
0
Ustilipid B
0
Ustilipid D1
0
Ustilipid D2
0
Ustilipid E1
0
Ustilipid E2
0
Ustilipid E3
0
Ustilipid F1
0
Ustilipid F2
0
Ustilipid F3
0
[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-5-[[(3R)-3-decanoyloxydodecanoyl]amino]-3,4-dihydroxy-6-phosphonooxyoxan-2-yl]methoxy]-3-[[(3R)-3-dodecanoyloxydodecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxyoxan-4-yl] (3R)-3-hydroxydodecanoate
0
[(2R,3S,4R,5R,6R)-5-[[(3R)-3-decanoyloxydodecanoyl]amino]-2-[[(2R,3R,4R,5S,6R)-3-[[(3R)-3-dodecanoyloxydodecanoyl]amino]-4-[(3R)-3-hydroxydodecanoyl]oxy-6-(hydroxymethyl)-5-phosphonooxyoxan-2-yl]oxymethyl]-3-hydroxy-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxydodecanoate
0
[(2R,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 7-methyloctanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 8-methylnonanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 9-methyldecanoate
0
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]methyl 3,4-dihydroxy-2-methylidenebutanoate
0
[(2r,3r,4s,5s,6r)-3-acetyloxy-2-(acetyloxymethyl)-5-hexanoyloxy-6-[(2s,3r)-2,3,4-trihydroxybutoxy]oxan-4-yl] tetradecanoate
0
[2-[4-Hydroxy-2,5-bis(hydroxymethyl)-3-(3-methylbutanoyloxy)oxolan-2-yl]oxy-6-(hydroxymethyl)-4,5-bis(2-methylpropanoyloxy)oxan-3-yl] decanoate
0
[3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoate
0
[6-[[6-[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-2-methylbut-2-enoate
0
alpha,alpha'-Trehalose 4,6-dioleate
0
alpha,alpha'-Trehalose 6,6'-dipalmitate
0
alpha,alpha'-Trehalose 6-palmitate
0
beta-D-Fructofuranosyl 4-O-(2-methylbutanoyl)-alpha-D-glucopyranoside
0
beta-D-Fructofuranosyl 4-O-decanoyl-alpha-D-glucopyranoside
0
beta-D-Fructofuranosyl 4-O-dodecanoyl-alpha-D-glucopyranoside
0
citrusoside A
0
citrusoside B
0
citrusoside C
0
citrusoside D
0
galactosyllipopolysaccharide +
0
glucosyllipopolysaccharide +
0
soldanelline B
0