mycophenolic acid
CHEBI:168396 EXACT SEEDED antiviralcytotoxic
A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
Structure
| Standard InChIKey | HPNSFSBZBAHARI-RUDMXATFSA-N |
|---|---|
| SMILES | COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA015757, pubchem:446541, chembl:CHEMBL866 |
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 4
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 brevicompactum NCBITaxon:5074 |
BGC_CHARACTERIZED | mibig:BGC0000104 | DOI:10.1128/aem.03015-10 |
| Penicillium roqueforti NCBITaxon:5082 |
BGC_CORRELATED | mibig:BGC0002616 | PMID:27889155 |
| Penicillium brevicompactum NCBITaxon:5074 |
BGC_CORRELATED | mibig:BGC0002619 | DOI:10.1128/aem.41.3.729-736.1981 |
| Penicillium roqueforti NCBITaxon:5082 |
SOURCE_ASSERTION | mibig:BGC0001677 | PMID:27889155 |
Occurrences 7
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 |
|---|---|---|
| Aspergillus NCBITaxon:5052 |
LOTUS | DOI:10.1042/BJ0500630 |
| Penicillium NCBITaxon:5073 |
LOTUS | DOI:10.1016/J.BMCL.2012.02.106 |
| Penicillium griseofulvum NCBITaxon:5078 |
LOTUS | DOI:10.1021/OL060107C |
| Penicillium echinulatum NCBITaxon:60174 |
LOTUS | DOI:10.1016/S0007-1536(88)80040-8 |
| Penicillium parvum NCBITaxon:70113 |
LOTUS | DOI:10.1021/NP8003497 |
| Penicillium brevicompactum NCBITaxon:5074 |
LOTUS | DOI:10.1128/AEM.03015-10 |
| Penicillium roqueforti NCBITaxon:5082 |
LOTUS | DOI:10.1016/J.FM.2016.10.013 |
Biosynthetic gene clusters 4
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000104 | Penicillium brevicompactum NCBITaxon:5074 |
CLUSTER_DEMONSTRATED | genbank:HQ731031.1 |
| mibig:BGC0002616 | Penicillium roqueforti NCBITaxon:5082 |
CLUSTER_CORRELATED | genbank:KU234531.1 |
| mibig:BGC0002619 | Penicillium brevicompactum NCBITaxon:5074 |
CLUSTER_CORRELATED | genbank:KM595305.1 |
| mibig:BGC0001677 | Penicillium roqueforti NCBITaxon:5082 |
CLUSTER_UNSTATED | genbank:KU234530.1 |
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 4 nodes, 3 edges
Mycophenolic acid inhibits human and Chinese hamster inosine-5'-monophosphate dehydrogenase isoforms.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| mycophenolic acid | inhibits | human inosine-5'-monophosphate dehydrogenase 1 | DOI:10.1021/jm070568j |
| mycophenolic acid | inhibits | human inosine-5'-monophosphate dehydrogenase 2 | DOI:10.1021/jm070568j |
| mycophenolic acid | inhibits | Chinese hamster inosine-5'-monophosphate dehydrogenase 2 | DOI:10.1016/S0092-8674(00)81275-1 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A Cell Based Secondary Assay To Explore Cytotoxicity of West Nile Virus Anti-Viral Hit Compounds | 4.61 uM | pubchem.aid:1650 |
| A Cell-Based Confirmatory Screen for Compounds that Inhibit VEEV, TC-83 | IC50 0.05 uM | pubchem.aid:588727 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 0.3663 uM | pubchem.aid:624296 |
| Acetylcholinesterase (AChE) small molecule antagonists: fluorescence cell-based qHTS assay | 43.6486 uM | pubchem.aid:1347398 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 1.0484 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 1.3198 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 1.4809 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 0.7422 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 1.3198 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 1.1763 uM | pubchem.aid:2202231 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 0.8327 uM | pubchem.aid:2202235 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 1.1883 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 1.496 uM | pubchem.aid:1346981 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 0.7308 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 3.1623 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 14.1254 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 0.2897 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 3.0962 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 0.4592 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 3.0962 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 0.3251 uM | pubchem.aid:2202551 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 2.1919 uM | pubchem.aid:2202551 |
| Confirmation Concentration-Response Assay for Enhancers of SMN2 Splice Variant Expression | 0.1585 uM | pubchem.aid:1740 |
| Confirmation Concentration-Response Assay for Enhancers of SMN2 Splice Variant Expression | 0.1 uM | pubchem.aid:1740 |
| Confirmation Concentration-Response Assay for Enhancers of SMN2 Splice Variant Expression | 0.3548 uM | pubchem.aid:1740 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:168396 (same structure, same inchikey)
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000104, BGC0001677, BGC0002616, BGC0002619. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000104 | MIBIG | 4 |
| BGC0002616 | MIBIG | 2 |
| BGC0002619 | MIBIG | 2 |
| BGC0001677 | MIBIG | 3 |
| CHEBI:168396 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/mycophenolic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.