doxorubicin
CHEBI:28748 EXACT SEEDED antimicrobial unspecifiedcytotoxicenzyme inhibitor
Structure
| Standard InChIKey | AOJJSUZBOXZQNB-TZSSRYMLSA-N |
|---|---|
| SMILES | C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:31703 |
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, 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 |
|---|---|---|---|
| Streptomyces peucetius NCBITaxon:1950 |
SOURCE_ASSERTION | mibig:BGC0000218 | PMID:7828855 |
Occurrences 25
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 |
|---|---|---|
| Xylopia aromatica NCBITaxon:1005655 |
LOTUS | DOI:10.1021/NP50106A007 |
| Moorea producens NCBITaxon:1155739 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B00549 |
| Oscillatoria NCBITaxon:1158 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B01147 |
| Trichodesmium thiebautii NCBITaxon:1208 |
LOTUS | DOI:10.1021/ACS.JNATPROD.0C00550 |
| Ochrolechia parella NCBITaxon:129506 |
LOTUS | DOI:10.1021/NP060561P |
| Annona muricata NCBITaxon:13337 |
LOTUS | DOI:10.1021/NP0105578 |
| Annona muricata NCBITaxon:13337 |
LOTUS | DOI:10.1021/NP50120A002 |
| Annona muricata NCBITaxon:13337 |
LOTUS | DOI:10.1021/NP50123A015 |
| Aspergillus sclerotiorum NCBITaxon:138282 |
LOTUS | DOI:10.1021/ACS.JNATPROD.5B00961 |
| Talaromyces aculeatus NCBITaxon:1392253 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00417 |
| Okeania NCBITaxon:1458928 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B01147 |
| Ophioparma ventosa NCBITaxon:145978 |
LOTUS | DOI:10.1021/ACS.JNATPROD.5B01073 |
| Viola abyssinica NCBITaxon:1471369 |
LOTUS | DOI:10.1021/NP100790F |
| Dendrodochium NCBITaxon:1502939 |
LOTUS | DOI:10.1021/NP500024R |
| Beta vulgaris NCBITaxon:161934 |
LOTUS | DOI:10.1016/J.JFF.2012.04.008 |
| Fusarium solani NCBITaxon:169388 |
LOTUS | DOI:10.1021/ACS.JNATPROD.6B00610 |
| Pestalotiopsis palmarum NCBITaxon:173185 |
LOTUS | DOI:10.1016/J.BMCL.2017.11.044 |
| Dracocephalum kotschyi NCBITaxon:180015 |
LOTUS | DOI:10.1016/J.PHYTOCHEM.2005.04.035 |
| Verrucosispora NCBITaxon:1873 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B00654 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/ACS.JNATPROD.6B01059 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/ACS.JNATPROD.6B01136 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00136 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B00481 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B01011 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/NP030212K |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000218 | Streptomyces peucetius NCBITaxon:1950 |
CLUSTER_UNSTATED | genbank:L35560.1 |
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 |
|---|---|---|
| A549 Cytotoxicity Assay Measured in Cell-Based System Using Plate Reader - 7071-06_Inhibitor_Dose_DryPowder_Activity_Set12 | 0.333 uM | pubchem.aid:743472 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 0.1864 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 0.1864 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 0.132 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 0.0372 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 0.0468 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 0.8327 uM | pubchem.aid:2202231 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 0.0934 uM | pubchem.aid:2202235 |
| Cell Proliferation Assay against the TMD8 Cell Line (Caspase readout at 16 hrs) | 0.0372 uM | pubchem.aid:651712 |
| Cell Proliferation Assay against the TMD8 Cell Line (Caspase readout at 8 hrs) | 3.3173 uM | pubchem.aid:651713 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 7.0795 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 0.8913 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 0.3474 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 0.4907 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 0.1099 uM | pubchem.aid:2202551 |
| Confirmatory qHTS to identify inhibitors of SARS-CoV-2 cell entry | 0.1918 uM | pubchem.aid:1645844 |
| Cytotoxicity counterscreen for NFkB agonists and antagonists | 0.0332 uM | pubchem.aid:624476 |
| HepG2 Cytotoxicity Assay Measured in Cell-Based System Using Plate Reader - 7071-02_Inhibitor_Dose_DryPowder_Activity_Set12 | 0.0577 uM | pubchem.aid:743471 |
| Identifying Small Molecule Inhibitors of Pancreatic Cancer Stem Cells (A2780, Spheroid) | 1.6626 uM | pubchem.aid:1259357 |
| Identifying Small Molecule Inhibitors of Pancreatic Cancer Stem Cells (Panc1, Adherent) | 9.3495 uM | pubchem.aid:1259362 |
| Identifying Small Molecule Inhibitors of Pancreatic Cancer Stem Cells (Panc1, Spheroid) | 5.8992 uM | pubchem.aid:1259359 |
| Identifying Small Molecule Inhibitors of Pancreatic Cancer Stem Cells (SN12C, Adherent) | 3.3173 uM | pubchem.aid:1259358 |
| Identifying Small Molecule Inhibitors of Pancreatic Cancer Stem Cells (SN12C, Spheroid) | 18.6548 uM | pubchem.aid:1259360 |
| Immunotoxin (HA22) sensitization/mitigation study - treatment arm (High Dose) | 16.6261 uM | pubchem.aid:1159530 |
| Immunotoxin (HA22) sensitization/mitigation study - treatment arm (low dose) | 0.0074 uM | pubchem.aid:1159512 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:28748 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000218 | MIBIG | 5 |
| CHEBI:28748 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/doxorubicin.yaml, which is generated from the committed inventories. Neither is edited by hand.