epothilone B
CHEBI:31550 EXACT SEEDED cytotoxicenzyme inhibitor
An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).
Structure
| Standard InChIKey | QXRSDHAAWVKZLJ-PVYNADRNSA-N |
|---|---|
| SMILES | C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C1=CSC(C)=N1 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA06085, pubchem:448013 |
Filing pathway
Unclassified — 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 nrps, pks, from MIBiG.
Producer organisms 4
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 |
|---|---|---|---|
| Sorangium cellulosum NCBITaxon:56 |
SOURCE_ASSERTION | mibig:BGC0000988 | PMID:10662695 |
| Sorangium cellulosum So0157-2 NCBITaxon:1254432 |
SOURCE_ASSERTION | mibig:BGC0000989 | PMID:23549746 |
| Sorangium cellulosum NCBITaxon:56 |
SOURCE_ASSERTION | mibig:BGC0000990 | PMID:10662695 |
| Sorangium cellulosum NCBITaxon:56 |
SOURCE_ASSERTION | mibig:BGC0000991 | PMID:10649995 |
Occurrences 11
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 |
|---|---|---|
| Microporus NCBITaxon:1191098 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00764 |
| Sparticola junci NCBITaxon:1803578 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B00604 |
| Nocardiopsis NCBITaxon:2013 |
LOTUS | DOI:10.1021/ACS.JNATPROD.8B00708 |
| Sporormiella similis NCBITaxon:269685 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00064 |
| Sorangium NCBITaxon:39643 |
LOTUS | DOI:10.1021/NP000629F |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.1002/ANIE.199615671 |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.1007/S00253-013-4830-0 |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.1016/S0378-1119(00)00149-9 |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.1016/S1074-5521(00)00075-2 |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.1021/NP000629F |
| Sorangium cellulosum NCBITaxon:56 |
LOTUS | DOI:10.7164/ANTIBIOTICS.49.560 |
Biosynthetic gene clusters 4
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000988 | Sorangium cellulosum NCBITaxon:56 |
CLUSTER_UNSTATED | genbank:AF210843.1 |
| mibig:BGC0000989 | Sorangium cellulosum So0157-2 NCBITaxon:1254432 |
CLUSTER_UNSTATED | genbank:EU414841.1 |
| mibig:BGC0000990 | Sorangium cellulosum NCBITaxon:56 |
CLUSTER_UNSTATED | genbank:GU063811.1 |
| mibig:BGC0000991 | Sorangium cellulosum NCBITaxon:56 |
CLUSTER_UNSTATED | genbank:AF217189.1 |
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.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 3.3498 uM | pubchem.aid:624297 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 0.0105 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 0.0118 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 0.0083 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 0.0093 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 0.0059 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 0.0186 uM | pubchem.aid:2202231 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 0.0059 uM | pubchem.aid:2202235 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 0.0282 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 0.0282 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 0.039 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 0.0693 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 0.0219 uM | pubchem.aid:2202551 |
| Confirmatory qHTS to identify inhibitors of SARS-CoV-2 cell entry | 0.0541 uM | pubchem.aid:1645844 |
| Human pregnane X receptor (PXR) activation by small molecules, qHTS assay | 7.9433 uM | pubchem.aid:1346985 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 0.0366 uM | PMID:31515284 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation | 0.0013 uM | pubchem.aid:504832 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 0.0013 uM | pubchem.aid:504834 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.0059 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.0059 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 0.0066 uM | pubchem.aid:1645876 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 0.0066 uM | pubchem.aid:1645876 |
| Rat pregnane X receptor (rPXR) activation by small molecules, qHTS assay | 10 uM | pubchem.aid:1346983 |
| S16 Schwann cell PMP22 intronic element beta-lactamase assay | 0.0112 uM | pubchem.aid:624044 |
| S16 Schwann cell PMP22 intronic element firefly luciferase assay | 0.0573 uM | pubchem.aid:624032 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000988, BGC0000989, BGC0000990, BGC0000991. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000988 | MIBIG | 5 |
| BGC0000989 | MIBIG | 3 |
| BGC0000990 | MIBIG | 3 |
| BGC0000991 | MIBIG | 4 |
| CHEBI:31550 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/epothilone-b.yaml, which is generated from the committed inventories. Neither is edited by hand.