erythromycin A
CHEBI:42355 EXACT SEEDED antibacterialcytotoxicenzyme inhibitor
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 against the primary literature, 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.
Causal graph — biosynthesis 8 nodes, 6 edges
Partial Saccharopolyspora erythraea NRRL 2338 erythromycin A biosynthesis graph for three curated tailoring enzymes.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| 6-deoxyerythronolide B | is hydroxylated by | EryF | DOI:10.1128/jb.174.3.725-735.1992 |
| EryF | forms | erythronolide B | 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
| Assay | Result | Reference |
|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 1.636 uM | pubchem.aid:624297 |
| Confirmatory fluorescence-based thiol-reactive (MSTI) qHTS assay for identification of artifact compounds | 0.9698 uM | pubchem.aid:1845226 |
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | 3.4528 uM | pubchem.aid:1671201 |
| Cytochrome P450 Family 3 Subfamily A Member 4 (CYP3A4) small molecule antagonists: luciferase reporter qHTS assay | 3.4528 uM | pubchem.aid:1671201 |
| Dopamine D2 receptor (DRD2) small molecule antagonists, cell-based qHTS assay | 52.8704 uM | pubchem.aid:1963595 |
| Dopamine D2 receptor (DRD2) small molecule antagonists, cell-based qHTS assay | 52.8704 uM | 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 | 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 | pubchem.aid:651700 |
| Inhibitors of Secretory Acid Sphingomyelinase (S-ASM): qHTS | 70.7946 uM | pubchem.aid:504937 |
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus | EC50 0.06 uM | pubchem.aid:1900 |
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity | EC50 0.06 uM | pubchem.aid:1902 |
| Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus | EC50 0.06 uM | 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 | PMID:24126916 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 9.285 uM | 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 | pubchem.aid:1963645 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 125.892 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 125.892 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 0.7943 uM | pubchem.aid:1645887 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 0.7943 uM | pubchem.aid:1645887 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.0006 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.0006 uM | pubchem.aid:1963824 |
| qHTS Inhibitors of AmpC Beta-Lactamase (assay with detergent) | 1.9953 uM | pubchem.aid:485294 |
| qHTS Inhibitors of AmpC Beta-Lactamase (assay without detergent) | 39.8107 uM | pubchem.aid:485341 |
| qHTS assay for small molecule activators of the heat shock response signaling pathway - cell viability counter screen | 16.865 uM | pubchem.aid:743209 |
| qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway - cell viability counter screen | 52.8704 uM | pubchem.aid:743203 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:42355 (same structure, same inchikey)
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.