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
19922
chemical entity
19920
molecular entity
19920
polyatomic entity
19877
macromolecule
8809
biomacromolecule
8330
polysaccharide derivative
5123
lipopolysaccharide
4091
(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
wzy2 dependent polymer
0
Path 2
CHEBI ontology
19922
subatomic particle
19892
composite particle
19892
hadron
19920
baryon
19892
nucleon
19920
atomic nucleus
19892
atom
19892
main group element atom
19866
p-block element atom
19866
carbon group element atom
19805
carbon atom
19802
organic molecular entity
19775
heteroorganic entity
19556
organochalcogen compound
19315
organooxygen compound
19205
carbohydrates and carbohydrate derivatives
15294
carbohydrate
15294
polysaccharide
8216
polysaccharide derivative
5123
O-polysaccharide
4091
lipopolysaccharide
4091
(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
wzy2 dependent polymer
0