emodin
CHEBI:42223 EXACT SEEDED cytotoxic
A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.
Structure
| Standard InChIKey | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
|---|---|
| SMILES | CC1=CC(=C2C(=C1)C(=O)C3=CC(=CC(=C3C2=O)O)O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:3220 |
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 |
|---|---|---|---|
| Aspergillus nidulans FGSC A4 NCBITaxon:227321 |
BGC_CHARACTERIZED | mibig:BGC0000101 | PMID:19448638 |
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 |
|---|---|---|
| Rumex dentatus NCBITaxon:1006352 |
LOTUS | DOI:10.1016/0305-1978(93)90049-W |
| Rhamnus davurica NCBITaxon:105902 |
LOTUS | DOI:10.1021/NP010030V |
| Ventilago leiocarpa NCBITaxon:108868 |
LOTUS | DOI:10.1016/0378-8741(96)01397-9 |
| Ventilago leiocarpa NCBITaxon:108868 |
LOTUS | DOI:10.1016/S0031-9422(00)84996-1 |
| Ventilago leiocarpa NCBITaxon:108868 |
LOTUS | DOI:10.1021/NP000569D |
| Ventilago leiocarpa NCBITaxon:108868 |
LOTUS | DOI:10.1142/S0192415X96000189 |
| Guanomyces polythrix NCBITaxon:110160 |
LOTUS | DOI:10.1016/S0031-9422(01)00278-3 |
| Guanomyces polythrix NCBITaxon:110160 |
LOTUS | DOI:10.1021/NP990534H |
| Picramnia antidesma NCBITaxon:1129486 |
LOTUS | DOI:10.1016/S0031-9422(98)00354-9 |
| Picramnia antidesma NCBITaxon:1129486 |
LOTUS | DOI:10.1016/S0031-9422(98)00383-5 |
| Talaromyces brunneus NCBITaxon:1131644 |
LOTUS | DOI:10.1248/CPB.11.402 |
| Dendrobium thyrsiflorum NCBITaxon:117978 |
LOTUS | DOI:10.1016/J.PHYTOCHEM.2005.04.001 |
| Rheum ribes NCBITaxon:1207382 |
LOTUS | DOI:10.1080/13880200701575049 |
| Derris cuneifolia NCBITaxon:1225674 |
LOTUS | DOI:10.3987/COM-92-6288 |
| Derris cuneifolia NCBITaxon:1225674 |
LOTUS | DOI:10.3987/COM-95-7069 |
| Senna occidentalis NCBITaxon:126820 |
LOTUS | DOI:10.1002/HLCA.200900460 |
| Senna occidentalis NCBITaxon:126820 |
LOTUS | DOI:10.1021/JF970690Z |
| Senna occidentalis NCBITaxon:126820 |
LOTUS | DOI:10.1039/J39700001285 |
| Senna occidentalis NCBITaxon:126820 |
LOTUS | DOI:10.1248/CPB.33.971 |
| Senna occidentalis NCBITaxon:126820 |
LOTUS | DOI:10.1248/CPB.37.511 |
| Annona muricata NCBITaxon:13337 |
LOTUS | DOI:10.1007/S13197-014-1289-7 |
| Cichorium intybus NCBITaxon:13427 |
LOTUS | DOI:10.1016/S0278-6915(99)00027-7 |
| Rumex alpinus NCBITaxon:1351827 |
LOTUS | DOI:10.1007/BF00596663 |
| Rheum compactum NCBITaxon:137216 |
LOTUS | DOI:10.1016/0378-8741(84)90016-3 |
| Rheum hotaoense NCBITaxon:137217 |
LOTUS | DOI:10.1016/0378-8741(84)90016-3 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000101 | Aspergillus nidulans FGSC A4 NCBITaxon:227321 |
CLUSTER_DEMONSTRATED | genbank:BN001308.1 |
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.
Causal graph — bioactivity 3 nodes, 2 edges
Emodin inhibits maize and human casein kinase II alpha subunits.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| emodin | inhibits | maize casein kinase II subunit alpha | DOI:10.1074/jbc.m209367200 |
| emodin | inhibits | human casein kinase II subunit alpha | DOI:10.1042/bj20030674 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — bioactivity 2 nodes, 1 edges
Emodin binds and inhibits Helicobacter pylori FabZ, beta-hydroxyacyl-ACP dehydratase.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| emodin | inhibits | Helicobacter pylori FabZ | DOI:10.1186/1471-2180-9-91 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 6
| Target | Assay organism | Measurement | Reference |
|---|---|---|---|
| 3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ | Francisella tularensis NCBITaxon:263 |
IC50 43100 nM | PMID:26818694 |
| 3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ [1-175] UniProtKB:B1JQH1 |
Yersinia pestis NCBITaxon:632 |
IC50 29700 nM | PMID:26818694 |
| Casein kinase II subunit alpha UniProtKB:P28523 |
Zea mays NCBITaxon:4577 |
KI 1850 nM | PMID:12419810 |
| Casein kinase II subunit alpha UniProtKB:P68400 |
Homo sapiens NCBITaxon:9606 |
KI 1850 nM | PMID:12816539 |
| Procathepsin L UniProtKB:P07711 |
Homo sapiens NCBITaxon:9606 |
IC50 10000 nM | PMID:32852058 |
| Procathepsin L UniProtKB:P07711 |
Homo sapiens NCBITaxon:9606 |
EC50 200000 nM | PMID:32852058 |
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay | 0.0033 uM | pubchem.aid:1963586 |
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay | 0.0033 uM | pubchem.aid:1963586 |
| A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis | 20.079 uM | pubchem.aid:435019 |
| A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol | IC50 88.95 uM | pubchem.aid:449764 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 1.8356 uM | pubchem.aid:624296 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 25.929 uM | pubchem.aid:624297 |
| ABL1 kinase (ABL1-N-HiBiT) SDR gain of signal screen | 3.9317 uM | pubchem.aid:1963315 |
| ABL1 kinase (ABL1-N-HiBiT) SDR gain of signal screen | 3.9317 uM | pubchem.aid:1963315 |
| ABL1 kinase (ABL1-N-HiBiT) SDR gain of signal screen - plus ATP | 27.3014 uM | pubchem.aid:1963316 |
| ABL1 kinase (ABL1-N-HiBiT) SDR gain of signal screen - plus ATP | 27.3014 uM | pubchem.aid:1963316 |
| ABL1 kinase (ABL1-N-HiBiT) enzymatic inhibition screen - Functional assay | 34.3705 uM | pubchem.aid:1963317 |
| ABL1 kinase (ABL1-N-HiBiT) enzymatic inhibition screen - Functional assay | 34.3705 uM | pubchem.aid:1963317 |
| Acetylcholinesterase (AChE) small molecule antagonists: fluorescence cell-based qHTS assay | 15.5351 uM | pubchem.aid:1347398 |
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 30.6379 uM | pubchem.aid:2061107 |
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 30.6379 uM | pubchem.aid:2061107 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 16.6155 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 37.1975 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 37.1975 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 9.3436 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 20.9177 uM | pubchem.aid:2202231 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 33.5937 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 48.5577 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS assay | 15.0057 uM | pubchem.aid:1346978 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS assay | 15.0057 uM | pubchem.aid:1346978 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 26.6844 uM | pubchem.aid:1346981 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000101 | MIBIG | 5 |
| CHEBI:42223 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/emodin.yaml, which is generated from the committed inventories. Neither is edited by hand.