lipopolysaccharide

naturalproductmech:mibig-ad23b710ca MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

Structure

Standard InChIKey	YPXVSQSYDIMPDZ-AUUHBOKRSA-N
SMILES	CCCCCCCCCCCCCCCC1[C@H](OC([C@H]([C@@H]1OC(=O)CC(CCCCCCCCCCC)O)O)CO[C@H]2[C@H](C([C@@H](C(O2)CO[C@@]3(CC([C@H](C(O3)C(CO)O)O[C@H]4[C@@H](C([C@@H](C(O4)C(CO)O)OP(=O)(O)OP(=O)(O)OCCN)O[C@@H]5[C@@H](C([C@@H](C(O5)C(CO[C@@H]6[C@@H](C([C@](CO6)(C(CO)O)O)O)O)O)OP(=O)(O)O)O[C@@H]7C(C([C@@H](C(O7)CO[C@@H]8C(C([C@H](C(O8)CO)O)O)O)O)O[C@@H]9C(C([C@H](C(O9)CO)O)O)O[C@@H]1C(C([C@@H](C(O1)CO)O[C@@H]1C(C([C@H](C(O1)CO)O)OC1[C@@H](C(C([C@@H](O1)C)O[C@@H]1C(C([C@@H](C(O1)CO)O)O[C@@H]1C(C[C@H](C(O1)C)O)O)O[C@@H]1C(C([C@H](C(O1)CO)O)O)O)O)O)O)O)O[C@@H]1[C@H](C([C@@H](C(O1)CO)O)O)NC(=O)C)O)O)O)O[C@@]1(CC([C@H](C(O1)C(CO)O)O)O[C@@]1(CC([C@H](C(O1)C(CO)O)O)O)C(=O)O)C(=O)O)C(=O)O)OP(=O)(O)O)OC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)CP(=O)(O)O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:11970143

Filing pathway

Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is saccharide, from MIBiG.

Producer organisms 5

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Brucella melitensis NCBITaxon:29459	SOURCE_ASSERTION	mibig:BGC0000772	PMID:9784561
Escherichia coli NCBITaxon:562	SOURCE_ASSERTION	mibig:BGC0000773	PMID:7677991
Legionella pneumophila NCBITaxon:446	SOURCE_ASSERTION	mibig:BGC0000775	PMID:11043980
Escherichia coli NCBITaxon:562	SOURCE_ASSERTION	mibig:BGC0000776	PMID:12374825
Escherichia coli NCBITaxon:562	SOURCE_ASSERTION	mibig:BGC0000777	PMID:12374825

Occurrences 3

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Brucella melitensis NCBITaxon:29459	LOTUS	DOI:10.1128/IAI.66.11.5485-5493.1998
Escherichia coli NCBITaxon:562	LOTUS	DOI:10.1128/JB.175.1.148-158.1993
Escherichia coli NCBITaxon:562	LOTUS	DOI:10.1128/JB.184.21.5912-5925.2002

Biosynthetic gene clusters 5

Accession	Host	Locus evidence	Genome
mibig:BGC0000772	Brucella melitensis NCBITaxon:29459	CLUSTER_UNSTATED	genbank:AF047478.1
mibig:BGC0000773	Escherichia coli NCBITaxon:562	CLUSTER_UNSTATED	genbank:AF125322.1
mibig:BGC0000775	Legionella pneumophila NCBITaxon:446	CLUSTER_UNSTATED	genbank:AJ007311.1
mibig:BGC0000776	Escherichia coli NCBITaxon:562	CLUSTER_UNSTATED	genbank:AJ426044.2
mibig:BGC0000777	Escherichia coli NCBITaxon:562	CLUSTER_UNSTATED	genbank:AJ426045.2

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Mechanism & Biosynthesis Overview

Explore across X-Mech

AntibioticMech (lipopolysaccharide) ↗ MediaIngredientMech (naturalproductmech:mibig-ad23b710ca) ↗ TaxonMech: Brucella melitensis (NCBITaxon:29459) ↗ TaxonMech: Escherichia coli (NCBITaxon:562) ↗ TaxonMech: Legionella pneumophila (NCBITaxon:446) ↗ TaxonMech: Escherichia coli (NCBITaxon:562) ↗ PathwayMech (mibig:BGC0000772) ↗ PathwayMech (mibig:BGC0000773) ↗ PathwayMech (mibig:BGC0000775) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0000772, BGC0000773, BGC0000775, BGC0000776, BGC0000777. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0000772	MIBIG	5
BGC0000773	MIBIG	3
BGC0000775	MIBIG	3
BGC0000776	MIBIG	3
BGC0000777	MIBIG	3

This page is generated from data/natural_products/fatty_acids/lipopolysaccharide.yaml, which is generated from the committed inventories. Neither is edited by hand.