erythromycin C

CHEBI:64273 EXACT SEEDED antimicrobial unspecified

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.

Structure

Standard InChIKey	MWFRKHPRXPSWNT-QNPWSHAKSA-N
SMILES	CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
Stereochemistry	fully defined
Cross-references	npatlas:NPA09987, pubchem:441095

Filing pathway

Polyketides — 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, saccharide, from MIBiG.

Producer organisms 1

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
Saccharopolyspora erythraea NRRL 2338 NCBITaxon:405948	BGC_CHARACTERIZED	mibig:BGC0000055	PMID:11336289

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000055	Saccharopolyspora erythraea NRRL 2338 NCBITaxon:405948	CLUSTER_DEMONSTRATED	genbank:AM420293.1

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
10	EryF 6-deoxyerythronolide B hydroxylase UniProtKB:Q00441	RHEA:40299	CHEBI:16089 → CHEBI:27977	DOI:10.1128/jb.174.3.725-735.1992
20	EryK erythromycin C-12 hydroxylase UniProtKB:P48635	RHEA:32631	CHEBI:63677 → CHEBI:64258	DOI:10.1021/bi00006a006
30	EryG erythromycin 3''-O-methyltransferase UniProtKB:A4F7P5	RHEA:32647	CHEBI:64258 → CHEBI:64268	DOI:10.1128/jb.172.5.2541-2546.1990

Step 10: Partial tailoring view: EryF hydroxylates 6-deoxyerythronolide B to erythronolide B; uncurated glycosylation and deoxysugar steps between erythronolide B and erythromycin D are intentionally omitted.

Step 20: EryK hydroxylates erythromycin D to erythromycin C. The erythromycin B branch is excluded here because EryK does not accept erythromycin B efficiently.

Step 30: EryG methylates erythromycin C(1+) at the mycarosyl 3-O position to produce erythromycin A(1+) in RHEA:32647; this NaturalProductRecord remains grounded to neutral erythromycin C, CHEBI:64273 (and the sibling erythromycin A record to neutral CHEBI:42355).

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 8 nodes, 6 edges

Partial Saccharopolyspora erythraea NRRL 2338 BGC0000055 macrolide tailoring graph (intermediate glycosylation steps between erythronolide B and erythromycin D intentionally omitted): EryF 6-deoxyerythronolide B C-6 hydroxylation, EryK C-12 hydroxylation of erythromycin D to erythromycin C, and downstream EryG 3''-O-methylation of erythromycin C to erythromycin A.

Subject	Predicate	Object	Notes	Evidence
6-deoxyerythronolide B	is hydroxylated by	EryF		DOI:10.1128/jb.174.3.725-735.1992 reference DOI:10.1128/jb.174.3.725-735.1992 evidence type PRIMARY_EXPERIMENT notes EryF catalyzes RHEA:40299.
EryF	forms	erythronolide B	The full DEBS-to-glycosylated-macrolide route between erythronolide B and erythromycin D remains uncurated in this partial graph.	DOI:10.1128/jb.174.3.725-735.1992 reference DOI:10.1128/jb.174.3.725-735.1992 evidence type PRIMARY_EXPERIMENT notes EryF catalyzes RHEA:40299.
erythromycin D	is hydroxylated by	EryK		DOI:10.1021/bi00006a006 reference DOI:10.1021/bi00006a006 evidence type PRIMARY_EXPERIMENT notes EryK catalyzes RHEA:32631.
EryK	forms	erythromycin C		DOI:10.1021/bi00006a006 reference DOI:10.1021/bi00006a006 evidence type PRIMARY_EXPERIMENT notes EryK catalyzes RHEA:32631.
erythromycin C	is O-methylated by	EryG		DOI:10.1128/jb.172.5.2541-2546.1990 reference DOI:10.1128/jb.172.5.2541-2546.1990 evidence type PRIMARY_EXPERIMENT notes EryG catalyzes RHEA:32647.
EryG	forms	erythromycin A(1+)		DOI:10.1128/jb.172.5.2541-2546.1990 reference DOI:10.1128/jb.172.5.2541-2546.1990 evidence type PRIMARY_EXPERIMENT notes EryG catalyzes RHEA:32647, whose ChEBI participants are the pH 7.3 erythromycin cations.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:64273 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (erythromycin C) ↗ MediaIngredientMech (CHEBI:64273) ↗ TaxonMech: Saccharopolyspora erythraea NRRL 2338 (NCBITaxon:405948) ↗ PathwayMech (mibig:BGC0000055) ↗

Provenance

Source concept	Source	Version
BGC0000055	MIBIG	5
CHEBI:64273	CHEBI	3-star

This page is generated from data/natural_products/polyketides/erythromycin-c.yaml, which is generated from the committed inventories. Neither is edited by hand.