enterocin

naturalproductmech:mibig-5172626ac8 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	CTBBEXWJRAPJIZ-VHPBLNRZSA-N
SMILES	[H][C@]12C[C@@]3(O)[C@@H](C4=CC(OC)=CC(=O)O4)[C@](O)([C@H](C(=O)C4=CC=CC=C4)[C@@]3(O)C(=O)O1)[C@@H]2O
Stereochemistry	fully defined
Cross-references	npatlas:NPA09644, npatlas:NPA009644, pubchem:23654446

Filing pathway

Terpenoids — 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 pks, from MIBiG.

Producer organisms 2

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
Streptomyces maritimus NCBITaxon:115828	BGC_CHARACTERIZED	mibig:BGC0000220	PMID:24162851
Streptomyces sp. SCSIO 11863 NCBITaxon:1333476	BGC_CHARACTERIZED	mibig:BGC0002366	PMID:31657934

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
Didemnum NCBITaxon:107394	LOTUS	DOI:10.1021/JO951794G
Streptomyces NCBITaxon:1883	LOTUS	DOI:10.1002/MRC.4384
Streptomyces NCBITaxon:1883	LOTUS	DOI:10.1016/0040-4020(96)00391-2

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0000220	Streptomyces maritimus NCBITaxon:115828	CLUSTER_DEMONSTRATED	genbank:AF254925.1
mibig:BGC0002366	Streptomyces sp. SCSIO 11863 NCBITaxon:1333476	CLUSTER_DEMONSTRATED	genbank:MK388865.1

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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	EncM UniProtKB:Q9KHK2		ungrounded → ungrounded	DOI:10.1021/ol0255155

Step 1: This curates only the Streptomyces maritimus EncM flavin-mediated oxidation that initiates the Favorskii-type rearrangement in enterocin biosynthesis; the reactive poly-beta-carbonyl substrate and rearranged pathway intermediate remain ungrounded.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Partial Streptomyces maritimus enterocin biosynthesis graph for the EncM-catalyzed oxidation that triggers the Favorskii-type rearrangement.

Subject	Predicate	Object	Notes	Evidence
unrearranged poly-beta-carbonyl intermediate	is oxidized by	EncM	The direct EncM substrate is an unstable, unrearranged poly-beta-carbonyl rather than a ChEBI-grounded stable pathway intermediate.	DOI:10.1021/ol0255155 DOI:10.1038/nature12643 DOI:10.1016/s1074-5521(00)00044-2 https://www.uniprot.org/uniprotkb/Q9KHK2 https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 reference DOI:10.1021/ol0255155 evidence type PRIMARY_EXPERIMENT snippet Inactivation of either gene terminated enterocin production and caused the accumulation of four nonrearranged, nonmethylated polyketides. notes Xiang et al. inactivated encM and encK in the Streptomyces maritimus enterocin cluster and showed that these genes are needed for the Favorskii-like rearrangement in enterocin biosynthesis. reference DOI:10.1038/nature12643 evidence type PRIMARY_EXPERIMENT snippet EncM catalyses the peroxyflavin-independent oxygenation-dehydrogenation dual oxidation of a highly reactive poly(β-carbonyl) notes Teufel et al. biochemically and structurally characterized the EncM flavoenzyme oxidation that triggers the Favorskii-type rearrangement central to enterocin biosynthesis. reference DOI:10.1016/s1074-5521(00)00044-2 evidence type PRIMARY_EXPERIMENT snippet A 21.3 kb gene cluster encoding the biosynthesis of the enterocin and wailupemycin family of polyketides from 'S. maritimus' has been cloned and sequenced. notes Piel et al. cloned and sequenced GenBank AF254925.1, the Streptomyces maritimus enterocin biosynthetic gene cluster that contains encM. reference https://www.uniprot.org/uniprotkb/Q9KHK2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Unreviewed UniProtKB:Q9KHK2 is Streptomyces maritimus EncM, gene encM, length 464 aa, and cross-references EMBL AF254925 protein AAF81732.1. reference https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AAF81732.1 is the AF254925.1 encM coding sequence from the Streptomyces maritimus enterocin cluster and is sequence-identical to UniProtKB:Q9KHK2.
EncM	triggers	Favorskii-type rearrangement	EncM performs the dual oxidation that initiates the Favorskii-type rearrangement; EncK also acts before mature enterocin is formed.	DOI:10.1021/ol0255155 DOI:10.1038/nature12643 DOI:10.1016/s1074-5521(00)00044-2 https://www.uniprot.org/uniprotkb/Q9KHK2 https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 reference DOI:10.1021/ol0255155 evidence type PRIMARY_EXPERIMENT snippet Inactivation of either gene terminated enterocin production and caused the accumulation of four nonrearranged, nonmethylated polyketides. notes Xiang et al. inactivated encM and encK in the Streptomyces maritimus enterocin cluster and showed that these genes are needed for the Favorskii-like rearrangement in enterocin biosynthesis. reference DOI:10.1038/nature12643 evidence type PRIMARY_EXPERIMENT snippet EncM catalyses the peroxyflavin-independent oxygenation-dehydrogenation dual oxidation of a highly reactive poly(β-carbonyl) notes Teufel et al. biochemically and structurally characterized the EncM flavoenzyme oxidation that triggers the Favorskii-type rearrangement central to enterocin biosynthesis. reference DOI:10.1016/s1074-5521(00)00044-2 evidence type PRIMARY_EXPERIMENT snippet A 21.3 kb gene cluster encoding the biosynthesis of the enterocin and wailupemycin family of polyketides from 'S. maritimus' has been cloned and sequenced. notes Piel et al. cloned and sequenced GenBank AF254925.1, the Streptomyces maritimus enterocin biosynthetic gene cluster that contains encM. reference https://www.uniprot.org/uniprotkb/Q9KHK2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Unreviewed UniProtKB:Q9KHK2 is Streptomyces maritimus EncM, gene encM, length 464 aa, and cross-references EMBL AF254925 protein AAF81732.1. reference https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AAF81732.1 is the AF254925.1 encM coding sequence from the Streptomyces maritimus enterocin cluster and is sequence-identical to UniProtKB:Q9KHK2.
Favorskii-type rearrangement	forms	Favorskii-rearranged enterocin intermediate	The rearranged pathway intermediate is left ungrounded because the exact immediate product of EncM in vivo is not a stable public ChEBI term.	DOI:10.1021/ol0255155 DOI:10.1038/nature12643 DOI:10.1016/s1074-5521(00)00044-2 https://www.uniprot.org/uniprotkb/Q9KHK2 https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 reference DOI:10.1021/ol0255155 evidence type PRIMARY_EXPERIMENT snippet Inactivation of either gene terminated enterocin production and caused the accumulation of four nonrearranged, nonmethylated polyketides. notes Xiang et al. inactivated encM and encK in the Streptomyces maritimus enterocin cluster and showed that these genes are needed for the Favorskii-like rearrangement in enterocin biosynthesis. reference DOI:10.1038/nature12643 evidence type PRIMARY_EXPERIMENT snippet EncM catalyses the peroxyflavin-independent oxygenation-dehydrogenation dual oxidation of a highly reactive poly(β-carbonyl) notes Teufel et al. biochemically and structurally characterized the EncM flavoenzyme oxidation that triggers the Favorskii-type rearrangement central to enterocin biosynthesis. reference DOI:10.1016/s1074-5521(00)00044-2 evidence type PRIMARY_EXPERIMENT snippet A 21.3 kb gene cluster encoding the biosynthesis of the enterocin and wailupemycin family of polyketides from 'S. maritimus' has been cloned and sequenced. notes Piel et al. cloned and sequenced GenBank AF254925.1, the Streptomyces maritimus enterocin biosynthetic gene cluster that contains encM. reference https://www.uniprot.org/uniprotkb/Q9KHK2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Unreviewed UniProtKB:Q9KHK2 is Streptomyces maritimus EncM, gene encM, length 464 aa, and cross-references EMBL AF254925 protein AAF81732.1. reference https://www.ncbi.nlm.nih.gov/protein/AAF81732.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AAF81732.1 is the AF254925.1 encM coding sequence from the Streptomyces maritimus enterocin cluster and is sequence-identical to UniProtKB:Q9KHK2.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Explore across X-Mech

AntibioticMech (enterocin) ↗ MediaIngredientMech (naturalproductmech:mibig-5172626ac8) ↗ TaxonMech: Streptomyces maritimus (NCBITaxon:115828) ↗ TaxonMech: Streptomyces sp. SCSIO 11863 (NCBITaxon:1333476) ↗ PathwayMech (mibig:BGC0000220) ↗ PathwayMech (mibig:BGC0002366) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0000220, BGC0002366. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0000220	MIBIG	4
BGC0002366	MIBIG	2

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