o-orsellinic acid
CHEBI:32807 EXACT SEEDED enzyme inhibitor
A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group.
Structure
| Standard InChIKey | AMKYESDOVDKZKV-UHFFFAOYSA-N |
|---|---|
| SMILES | CC1=CC(=CC(=C1C(=O)O)O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:68072, npatlas:NPA024876, chembl:CHEMBL457583 |
Filing pathway
Shikimates and phenylpropanoids — 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, terpene, from MIBiG.
Producer organisms 5
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:BGC0000057 | PMID:20174687 |
| Fusarium graminearum PH-1 NCBITaxon:229533 |
BGC_CHARACTERIZED | mibig:BGC0002594 | PMID:25011010 |
| Colletotrichum higginsianum IMI 349063 NCBITaxon:759273 |
BGC_CORRELATED | mibig:BGC0002812 | DOI:10.1016/j.ymben.2023.10.002 |
| Moniliophthora roreri MCA 2997 NCBITaxon:1381753 |
SOURCE_ASSERTION | mibig:BGC0002212 | DOI:10.1126/sciadv.aar5459 |
| Claviceps purpurea 20.1 NCBITaxon:1111077 |
SOURCE_ASSERTION | mibig:BGC0002596 | PMID:33130255 |
Occurrences 22
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 |
|---|---|---|
| Nidularia pulvinata NCBITaxon:1081941 |
LOTUS | DOI:10.1515/ZNC-1997-5-606 |
| Hypoxylon rubiginosum NCBITaxon:110542 |
LOTUS | DOI:10.1021/NP040063L |
| Penicillium purpurogenum NCBITaxon:1266744 |
CHEBI | PMID:21879714 |
| Ascomycota sp. Ind19F07 NCBITaxon:1583058 |
CHEBI | PMID:25537370 |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1073/PNAS.0901870106 |
| Parmotrema stuppeum NCBITaxon:2041279 |
LOTUS | DOI:10.1515/ZNC-2000-11-1227 |
| Parmotrema tinctorum NCBITaxon:235862 |
LOTUS | DOI:10.4268/CJCMM20141620 |
| Dolichousnea longissima NCBITaxon:281306 |
LOTUS | DOI:10.1016/S0031-9422(00)82466-8 |
| Parmotrema cooperi NCBITaxon:2910500 |
LOTUS | DOI:10.1007/S11426-011-4436-2 |
| Aspergillus terreus NCBITaxon:33178 |
LOTUS | DOI:10.1016/J.PHYTOL.2015.02.009 |
| Aspergillus terreus NCBITaxon:33178 |
LOTUS | DOI:10.1039/C39720000391 |
| Penicillium aurantiogriseum NCBITaxon:36655 |
LOTUS | DOI:10.1039/C39920000646 |
| Chaetomium globosum NCBITaxon:38033 |
LOTUS | DOI:10.1021/NP058014B |
| Umbilicaria torrefacta NCBITaxon:392743 |
LOTUS | DOI:10.1016/0031-9422(90)83052-3 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1271/BBB.63.820 |
| Penicillium NCBITaxon:5073 |
LOTUS | DOI:10.1021/NP500885F |
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1073/PNAS.0901870106 |
| Penicillium cyclopium NCBITaxon:60167 |
LOTUS | DOI:10.1039/C39920000646 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1042/BJ0970321 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1042/BJ0980353 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1080/13693780802307720 |
| Stachybotrys cylindrospora NCBITaxon:80386 |
LOTUS | DOI:10.1139/V93-069 |
Biosynthetic gene clusters 5
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000057 | Aspergillus nidulans FGSC A4 NCBITaxon:227321 |
CLUSTER_DEMONSTRATED | genbank:AACD01000135.1 |
| mibig:BGC0002594 | Fusarium graminearum PH-1 NCBITaxon:229533 |
CLUSTER_DEMONSTRATED | genbank:CM000575.1 |
| mibig:BGC0002812 | Colletotrichum higginsianum IMI 349063 NCBITaxon:759273 |
CLUSTER_CORRELATED | genbank:LTAN01000004.1 |
| mibig:BGC0002212 | Moniliophthora roreri MCA 2997 NCBITaxon:1381753 |
CLUSTER_UNSTATED | genbank:AWSO01000045.1 |
| mibig:BGC0002596 | Claviceps purpurea 20.1 NCBITaxon:1111077 |
CLUSTER_UNSTATED | genbank:CAGA01000059.1 |
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 5
| Assay | Result | Reference |
|---|---|---|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 89.1251 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 89.1251 uM | pubchem.aid:1645883 |
| qHTS Assay for Activators of Cytochrome P450 3A4 | 25.1189 uM | pubchem.aid:885 |
| qHTS Assay for Inhibitors and Substrates of Cytochrome P450 3A4 | 25.1189 uM | pubchem.aid:884 |
| qHTS Assay for Inhibitors of the Human Apurinic/apyrimidinic Endonuclease 1 (APE1) | 0.0089 uM | pubchem.aid:2517 |
Open questions 2
name-disagreement — ChEBI calls this structure 'o-orsellinic acid' and MIBiG calls it 'Orsellinic acid', 'orsellinic acid'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000057, BGC0002212, BGC0002594, BGC0002596, BGC0002812. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000057 | MIBIG | 5 |
| BGC0002594 | MIBIG | 2 |
| BGC0002812 | MIBIG | 2 |
| BGC0002212 | MIBIG | 3 |
| BGC0002596 | MIBIG | 2 |
| CHEBI:32807 | CHEBI | 3-star |
This page is generated from data/natural_products/shikimates_and_phenylpropanoids/o-orsellinic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.