itaconic acid
CHEBI:30838 EXACT SEEDED cytotoxic
A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.
Structure
| Standard InChIKey | LVHBHZANLOWSRM-UHFFFAOYSA-N |
|---|---|
| SMILES | C=C(CC(=O)O)C(=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:811 |
Filing pathway
Fatty acids — 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 other, 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 |
|---|---|---|---|
| Ustilago maydis NCBITaxon:5270 |
SOURCE_ASSERTION | mibig:BGC0001286 | DOI:10.1038/s41598-021-97352-x |
Occurrences 18
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 |
|---|---|---|
| Pycnandra acuminata NCBITaxon:280718 |
LOTUS | DOI:10.1016/J.PHYTOCHEM.2007.07.001 |
| Arabidopsis thaliana NCBITaxon:3702 |
LOTUS | DOI:10.1073/PNAS.0609709104 |
| Arabidopsis thaliana NCBITaxon:3702 |
LOTUS | DOI:10.1111/PCE.12714 |
| Phaseolus vulgaris NCBITaxon:3885 |
LOTUS | DOI:10.3390/METABO4030599 |
| Vicia faba NCBITaxon:3906 |
LOTUS | DOI:10.1002/ELPS.201300646 |
| Vicia faba NCBITaxon:3906 |
LOTUS | DOI:10.1007/BF00381261 |
| Vicia faba NCBITaxon:3906 |
LOTUS | DOI:10.1016/J.PLAPHY.2015.04.008 |
| Vicia faba NCBITaxon:3906 |
LOTUS | DOI:10.1104/PP.69.2.522 |
| Solanum tuberosum NCBITaxon:4113 |
LOTUS | DOI:10.1016/J.PHYTOCHEM.2016.12.003 |
| Lilium longiflorum NCBITaxon:4690 |
LOTUS | DOI:10.1016/0031-9422(81)83095-6 |
| Caenorhabditis elegans NCBITaxon:6239 |
LOTUS | DOI:10.3389/FMOLB.2018.00096 |
| Ustilago cynodontis NCBITaxon:63396 |
LOTUS | DOI:10.1080/00021369.1990.10870333 |
| Ustilago cynodontis NCBITaxon:63396 |
LOTUS | DOI:10.1080/00021369.1990.10870334 |
| Ustilago cynodontis NCBITaxon:63396 |
LOTUS | DOI:10.1271/BBB1961.54.2359 |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1007/S11306-016-1051-4 |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1038/NBT.2488 |
| Homo sapiens NCBITaxon:9606 |
CHEBI | PMID:23610393 |
| Ustilago maydis NCBITaxon:5270 |
LOTUS | DOI:10.1111/1751-7915.12329 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001286 | Ustilago maydis NCBITaxon:5270 |
CLUSTER_UNSTATED | genbank:KT852988.1 |
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 22
| Assay | Result | Reference |
|---|---|---|
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 1.90226 uM | pubchem.aid:2061107 |
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 1.90226 uM | pubchem.aid:2061107 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 28.4485 uM | pubchem.aid:1346981 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 81.2025 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 81.2025 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 74.0014 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 74.0014 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 40.6977 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 40.6977 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay | 72.3718 uM | pubchem.aid:1671198 |
| Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay | 72.3718 uM | pubchem.aid:1671198 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes | 52.3416 uM | pubchem.aid:1963577 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes | 47.6849 uM | pubchem.aid:1963577 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary | 44.0399 uM | pubchem.aid:1963585 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary | 44.0399 uM | pubchem.aid:1963585 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary | 47.6849 uM | pubchem.aid:1963585 |
| p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary | 47.6849 uM | pubchem.aid:1963585 |
| qHTS assay for identifying genotoxic compounds that show differential cytotoxicity against isogenic chicken DT40 cell lines with known DNA damage response pathways - Rev3 mutant cell line | 78.4482 uM | pubchem.aid:743014 |
| qHTS assay to identify small molecule agonists of the farnesoid-X-receptor (FXR) signaling pathway - cell viability counter screen | 7.2071 uM | pubchem.aid:743218 |
| qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line | 13.9503 uM | pubchem.aid:743042 |
| qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screen | 11.1771 uM | pubchem.aid:743074 |
| qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway | 56.0183 uM | pubchem.aid:743215 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001286 | MIBIG | 3 |
| CHEBI:30838 | CHEBI | 3-star |
This page is generated from data/natural_products/fatty_acids/itaconic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.