NaturalProductMech

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itaconic acid

CHEBI:30838 EXACT SEEDED

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.

Structure

Standard InChIKeyLVHBHZANLOWSRM-UHFFFAOYSA-N
SMILESC=C(CC(=O)O)C(=O)O
Stereochemistryfully defined
Cross-referencespubchem: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.

TaxonBasisClusterEvidence
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.

TaxonSourceReference
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

AccessionHostLocus evidenceGenome
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.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 18 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT itaconic acid CHEBI:30838 Fatty acids TARGETS & BIOACTIVITY 0 molecular targets 22 bioactivities · 0 graphs

Bioactivities 22

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

AssayResultTarget enzymeSource detail
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: SummaryOTHER 1.90226 uM; NOT_DETERMINEDNot recorded
pubchem.aid:2061107
assay
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary
evidence
  • reference
    pubchem.aid:2061107
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2061107, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
1.90226
units
uM
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: SummaryOTHER 1.90226 uM; NOT_DETERMINEDNot recorded
pubchem.aid:2061107
assay
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary
evidence
  • reference
    pubchem.aid:2061107
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2061107, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_000015 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
1.90226
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 28.4485 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1346981
assay
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346981
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
28.4485
units
uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assayOTHER 81.2025 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671199
assay
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671199
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
81.2025
units
uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assayOTHER 81.2025 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671199
assay
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671199
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession EAW99313 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
81.2025
units
uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assayOTHER 74.0014 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671199
assay
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671199
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
74.0014
units
uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assayOTHER 74.0014 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671199
assay
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671199
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession EAW99313 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
74.0014
units
uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assayOTHER 40.6977 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671197
assay
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671197
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
40.6977
units
uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assayOTHER 40.6977 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671197
assay
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671197
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAV41877 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
40.6977
units
uM
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assayOTHER 72.3718 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671198
assay
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671198
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671198, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
72.3718
units
uM
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assayOTHER 72.3718 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671198
assay
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay
evidence
  • reference
    pubchem.aid:1671198
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671198, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AGS09764 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
72.3718
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomesOTHER 52.3416 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963577
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes
evidence
  • reference
    pubchem.aid:1963577
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963577, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AFN61604 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
52.3416
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomesOTHER 47.6849 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963577
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes
evidence
  • reference
    pubchem.aid:1963577
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963577, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AFN61604 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
47.6849
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: SummaryOTHER 44.0399 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963585
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary
evidence
  • reference
    pubchem.aid:1963585
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963585, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
44.0399
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: SummaryOTHER 44.0399 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963585
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary
evidence
  • reference
    pubchem.aid:1963585
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963585, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AFN61604 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
44.0399
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: SummaryOTHER 47.6849 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963585
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary
evidence
  • reference
    pubchem.aid:1963585
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963585, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
47.6849
units
uM
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: SummaryOTHER 47.6849 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963585
assay
p53 small molecule agonists, cell-based qHTS assay with human liver microsomes: Summary
evidence
  • reference
    pubchem.aid:1963585
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963585, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AFN61604 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
47.6849
units
uM
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 lineOTHER 78.4482 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743014
assay
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
evidence
  • reference
    pubchem.aid:743014
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743014, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
78.4482
units
uM
qHTS assay to identify small molecule agonists of the farnesoid-X-receptor (FXR) signaling pathway - cell viability counter screenOTHER 7.2071 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743218
assay
qHTS assay to identify small molecule agonists of the farnesoid-X-receptor (FXR) signaling pathway - cell viability counter screen
evidence
  • reference
    pubchem.aid:743218
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743218, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
7.2071
units
uM
qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell lineOTHER 13.9503 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743042
assay
qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line
evidence
  • reference
    pubchem.aid:743042
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743042, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAI32976 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
13.9503
units
uM
qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screenOTHER 11.1771 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743074
assay
qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screen
evidence
  • reference
    pubchem.aid:743074
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743074, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
11.1771
units
uM
qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathwayOTHER 56.0183 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743215
assay
qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway
evidence
  • reference
    pubchem.aid:743215
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743215, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession BAH02282 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
56.0183
units
uM

Explore across X-Mech

AntibioticMech (itaconic acid) ↗ MediaIngredientMech (CHEBI:30838) ↗ TaxonMech: Ustilago maydis (NCBITaxon:5270) ↗ PathwayMech (mibig:BGC0001286) ↗

Provenance

Source conceptSourceVersion
BGC0001286MIBIG3
CHEBI:30838CHEBI3-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.