erythromycin A
CHEBI:42355 EXACT SEEDED antibacterialcytotoxicenzyme inhibitor
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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-3-O-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 | ULGZDMOVFRHVEP-RWJQBGPGSA-N |
|---|---|
| SMILES | CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:12560, chembl:CHEMBL532 |
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 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 |
|---|---|---|---|
| Saccharopolyspora erythraea NRRL 2338 NCBITaxon:405948 |
BGC_CHARACTERIZED | mibig:BGC0000055 | PMID:11336289 |
| Aeromicrobium erythreum NCBITaxon:2041 |
SOURCE_ASSERTION | mibig:BGC0000054 | PMID:15257441 |
Occurrences 14
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 |
|---|---|---|
| Bacillus subtilis NCBITaxon:1423 |
LOTUS | DOI:10.1021/ACSCATAL.1C05131 |
| Saccharopolyspora erythraea NCBITaxon:1836 |
LOTUS | DOI:10.1016/0021-9673(91)80132-Z |
| Saccharopolyspora erythraea NCBITaxon:1836 |
LOTUS | DOI:10.1016/0040-4039(91)80057-D |
| Saccharopolyspora erythraea NCBITaxon:1836 |
LOTUS | DOI:10.1021/ACSSYNBIO.8B00372 |
| Saccharopolyspora erythraea NCBITaxon:1836 |
LOTUS | DOI:10.1248/CPB.42.1522 |
| Saccharopolyspora erythraea NCBITaxon:1836 |
LOTUS | DOI:10.7164/ANTIBIOTICS.40.1115 |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1021/BI965010K |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1021/BI965010K |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1021/NP400145U |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/BF00873025 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1038/SREP44786 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.4103/0250-474X.42979 |
| Pseudoalteromonas NCBITaxon:53246 |
LOTUS | DOI:10.1021/NP500775E |
| Aeromicrobium erythreum NCBITaxon:2041 |
LOTUS | DOI:10.1007/S10295-004-0154-5 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000055 | Saccharopolyspora erythraea NRRL 2338 NCBITaxon:405948 |
CLUSTER_DEMONSTRATED | genbank:AM420293.1 |
| mibig:BGC0000054 | Aeromicrobium erythreum NCBITaxon:2041 |
CLUSTER_UNSTATED | genbank:AY623658.2 |
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.
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 A, CHEBI:42355.
Mechanism & Biosynthesis Overview
Causal graph — biosynthesis 8 nodes, 6 edges
Partial Saccharopolyspora erythraea NRRL 2338 erythromycin A biosynthesis graph for three curated tailoring enzymes.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| 6-deoxyerythronolide B | is hydroxylated by | EryF | DOI:10.1128/jb.174.3.725-735.1992
|
|
| 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
|
| erythromycin D | is hydroxylated by | EryK | DOI:10.1021/bi00006a006
|
|
| EryK | forms | erythromycin C | DOI:10.1021/bi00006a006
|
|
| erythromycin C | is O-methylated by | EryG | DOI:10.1128/jb.172.5.2541-2546.1990
|
|
| EryG | forms | erythromycin A(1+) | DOI:10.1128/jb.172.5.2541-2546.1990
|
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.
| Assay | Result | Target enzyme | Source detail |
|---|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | OTHER 1.636 uM; NOT_DETERMINED | Not recorded | pubchem.aid:624297
|
| Confirmatory fluorescence-based thiol-reactive (MSTI) qHTS assay for identification of artifact compounds | OTHER 0.9698 uM; INACTIVE | Not recorded | pubchem.aid:1845226
|
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | OTHER 3.4528 uM; ACTIVE | Not recorded | pubchem.aid:1671201
|
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | OTHER 3.4528 uM; ACTIVE | Not recorded | pubchem.aid:1671201
|
| Dopamine D2 receptor (DRD2) small molecule antagonists, cell-based qHTS assay | OTHER 52.8704 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1963595
|
| Dopamine D2 receptor (DRD2) small molecule antagonists, cell-based qHTS assay | OTHER 52.8704 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1963595
|
| Dose response confirmation of small molecule inhibitors of Low Molecular Weight Protein Tyrosine Phosphatase, LMPTP, in an orthogonal absorbance-based assay | IC50 80 uM; INACTIVE | Not recorded | pubchem.aid:652005
|
| Dose response confirmation of small molecule inhibitors of Low Molecular Weight Protein Tyrosine Phosphatase, LMPTP, via a fluorescence intensity assay | IC50 47.1 uM; INACTIVE | UniProtKB:P24666 | pubchem.aid:651700
|
| Inhibitors of Secretory Acid Sphingomyelinase (S-ASM): qHTS | OTHER 70.7946 uM; NOT_DETERMINED | Not recorded | pubchem.aid:504937
|
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus | EC50 0.06 uM; ACTIVE | Not recorded | pubchem.aid:1900
|
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity | EC50 0.06 uM; ACTIVE | Not recorded | pubchem.aid:1902
|
| Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus | EC50 0.06 uM; ACTIVE | Not recorded | pubchem.aid:1915
|
| Oatp1d1 Transport Assay from Article 10.1074/jbc.M113.518506: "Molecular characterization of zebrafish Oatp1d1 (Slco1d1), a novel organic anion-transporting polypeptide." | KI 882 uM; INACTIVE | Not recorded | PMID:24126916
|
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | OTHER 9.285 uM; NOT_DETERMINED | Not recorded | pubchem.aid:504834
|
| Surface Plasmon Resonance (SPR) from US Patent US20240118263: "TARGET FOR SCREENING ANTI-TUMOR DRUG, USE THEREOF AND SCREENING METHOD THEREFOR" | KD 10.4 uM; INACTIVE | UniProtKB:Q8IZQ5 | pubchem.aid:1963645
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 125.892 uM; INACTIVE | Not recorded | pubchem.aid:1645883
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 125.892 uM; INACTIVE | UniProtKB:O95398 | pubchem.aid:1645883
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | OTHER 0.7943 uM; INACTIVE | Not recorded | pubchem.aid:1645887
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | OTHER 0.7943 uM; INACTIVE | UniProtKB:Q8WZA2 | pubchem.aid:1645887
|
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | OTHER 0.0006 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1963824
|
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | OTHER 0.0006 uM; NOT_DETERMINED | UniProtKB:P43405 | pubchem.aid:1963824
|
| qHTS Inhibitors of AmpC Beta-Lactamase (assay with detergent) | OTHER 1.9953 uM; NOT_DETERMINED | Not recorded | pubchem.aid:485294
|
| qHTS Inhibitors of AmpC Beta-Lactamase (assay without detergent) | OTHER 39.8107 uM; INACTIVE | Not recorded | pubchem.aid:485341
|
| qHTS assay for small molecule activators of the heat shock response signaling pathway - cell viability counter screen | OTHER 16.865 uM; NOT_DETERMINED | Not recorded | pubchem.aid:743209
|
| qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway - cell viability counter screen | OTHER 52.8704 uM; NOT_DETERMINED | Not recorded | pubchem.aid:743203
|
Elsewhere in the fleet
- AntibioticMech — CHEBI:42355 (same structure, same inchikey)
Explore across X-Mech
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000054, BGC0000055. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000055 | MIBIG | 5 |
| BGC0000054 | MIBIG | 5 |
| CHEBI:42355 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/erythromycin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.