mevinic acid
CHEBI:39508 EXACT SEEDED cytotoxicenzyme inhibitor
A member of the class of hexahydronaphthalenes that is 1,2,6,7,8,8a-hexahydronaphthalene which is substituted by a (3R,5R)-6-carboxy-3,5-dihydroxyhexyl group at position 1, a methyl group at position 2, and a (2S)-2-methylbutanoyloxy group at position 8 (the 1S,2S,8S,8aR isomer). Lactonisation of the hydroxy-carboxylic acid chain at position 1 affords mevastatin.
Structure
| Standard InChIKey | BOZILQFLQYBIIY-INTXDZFKSA-N |
|---|---|
| SMILES | CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA018102, pubchem:64715 |
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 |
|---|---|---|---|
| Penicillium citrinum NCBITaxon:5077 |
SOURCE_ASSERTION | mibig:BGC0000039 | PMID:12172803 |
Occurrences 3
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 |
|---|---|---|
| Penicillium javanicum NCBITaxon:28578 |
LOTUS | DOI:10.1021/NP040052S |
| Penicillium javanicum NCBITaxon:28578 |
LOTUS | DOI:10.1039/P19760001165 |
| Penicillium citrinum NCBITaxon:5077 |
LOTUS | DOI:10.1007/S00438-002-0697-Y |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000039 | Penicillium citrinum NCBITaxon:5077 |
CLUSTER_UNSTATED | genbank:AB072893.1 |
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 |
|---|---|---|
| A Quantitative High throughput Screen to Identify Chemical Modulators of PINK1 Expression | 12.5893 uM | pubchem.aid:624263 |
| A Quantitative High throughput Screen to Identify Chemical Modulators of PINK1 Expression | 12.5893 uM | pubchem.aid:624263 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 7.3078 uM | pubchem.aid:624296 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 3.2643 uM | pubchem.aid:624297 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 10.4837 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 18.6429 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 18.6429 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 18.6429 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 11.7629 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 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 14.8086 uM | pubchem.aid:2202235 |
| Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome | 12.5893 uM | PMID:33910017 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 17.7828 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 4.9071 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 9.791 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 9.791 uM | pubchem.aid:2202551 |
| Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 7.9433 uM | PMID:33910017 |
| Confirmatory qHTS to identify inhibitors of SARS-CoV-2 cell entry | 1.9182 uM | pubchem.aid:1645844 |
| Counterscreen for inhibitors of NLG for Luciferase Activators Measured in Cell-Based System Using Plate Reader - 2146-03_Inhibitor_Dose_CherryPick_Activity | 1.26 uM | pubchem.aid:624404 |
| Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay | 50.1187 uM | PMID:33910017 |
| Cytometry Cell-Based qHTS for Inhibitors of the mTORC1 Signaling Pathway in MEF cells | 9.2683 uM | pubchem.aid:2668 |
| HTS Assay for Allosteric Agonists of the Human D1 Dopamine Receptor: Primary Screen for Potentiators | 4.1092 uM | pubchem.aid:488982 |
| High Content Imaging Cell-Based qHTS for Inhibitors of the mTORC1 Signaling Pathway in MEF Cells | 16.4816 uM | pubchem.aid:2667 |
| Luciferase Reporter Cell Based HTS to identify inhibitors of N-linked Glycosylation Measured in Cell-Based System Using Plate Reader - 2146-01_Inhibitor_Dose_CherryPick_Activity | 0.18 uM | pubchem.aid:624491 |
| Nrf2 qHTS screen for inhibitors | 18.3564 uM | pubchem.aid:504444 |
Open questions 1
name-disagreement — ChEBI calls this structure 'mevinic acid' and MIBiG calls it 'compactin'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000039 | MIBIG | 3 |
| CHEBI:39508 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/mevinic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.