mycophenolic acid

CHEBI:168396 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:25384
Label unavailable CHEBI:33853
Label unavailable CHEBI:37581
Label unavailable CHEBI:38831

Chemical structure

Computed structure properties
Molecular formula	C17H20O6
Charge	0
Average mass	320.341 Da
Monoisotopic mass	320.12599 Da
Source	ChEBI
InChIKey	HPNSFSBZBAHARI-RUDMXATFSA-N

SMILES

COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2

InChI

InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+

Also called

acide mycophenolique (INN)— chebi
acido micofenolico (INN)— chebi
acidum mycophenolicum (INN)— chebi
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid (EXACT_SYNONYM)— chebi
(E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid (EXACT_SYNONYM)— chebi
Micofenolico acido (EXACT_SYNONYM)— chebi
Mycophenolate (EXACT_SYNONYM)— chebi
Mycophenolsäure (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:24280-93-1
pdb-ccd:MOA
reaxys:318158

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

anticoronaviral agent CHEBI:149553
antimicrobial agent CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:168396`	mycophenolic acid	`antibioticmech:chebi-d2a5e263f3`	2026-08-30

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
RPB1-associated laboratory mycophenolic-acid resistance (qualified association) Selected RPB1 laboratory comparisons are labeled resistant in Figure 2D; Figure 2A provides matched growth controls. Other RPB1 comparisons are sensitive or have baseline growth defects. This is not a shared effect of all RPB1 alleles, a clinical resistance category, an MIC, or a species-wide phenotype. Text S1 identifies S288C-derived backgrounds and CKY283 as the genetic-comparison parent, not as an identifier for every tested derivative. RPB1 is the paper's name for RPO21. UniProtKB:P04050 and NCBITaxon:559292 identify S288c reference context only; no exact experimental protein, allele, strain TaxID or genome is assigned. The accompanying IMD transcription results do not make Rpb1 a direct drug target; the Figure 5A probe is not uniquely IMD2-specific.	—	Saccharomyces cerevisiae `NCBITaxon:4932`	RPB1	DOI:10.1371/journal.pgen.1002627 (Kaplan et al. 2012: Figure 2A/D, Results and Discussion, Tables S1/S2 and Text S1. Native figures and rendered supplements inspected. Viability in Table S1 is not an independent drug-resistance endpoint; growth and purified-enzyme contexts remain distinct.) UniProtKB:P04050 (Reference-only RPO21/RPB1, YDL140C, SGD:S000002299; UniProt release 2026_03, entry version 255, sequence version 2, retrieved 2026-10-14. S288c reference taxon 559292 belongs to species 4932 in cached UniProt Taxonomy. These are not tested derivative or mutant-specific accessions.) Comparative plate-growth assay

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Penicillium brevicompactum NCBITaxon:5074	BGC0000104	Knock-out studies compound specific	MIBIG 4.0.1 (entry 4)	questionable	MIBiG active entry; compound 'mycophenolic acid' joined by exact Standard InChIKey.	DOI:10.1128/aem.03015-10 (MIBiG attaches this reference to the compound, as support for its STRUCTURE: every compound-level method in the release is structure elucidation (NMR, mass spectrometry, X-ray, total synthesis). It establishes what the molecule is. It is NOT evidence that this organism produces it; MIBiG attaches no reference to the producer link at all.)
Penicillium roqueforti NCBITaxon:5082	BGC0002616	Gene expression correlated with compound production compound specific	MIBIG 4.0.1 (entry 2)	questionable	MIBiG active entry; compound 'mycophenolic acid' joined by exact Standard InChIKey.	PMID:27889155 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)
Penicillium brevicompactum NCBITaxon:5074	BGC0002619	Gene expression correlated with compound production compound specific	MIBIG 4.0.1 (entry 2)	questionable	MIBiG active entry; compound 'mycophenolic acid' joined by exact Standard InChIKey.	DOI:10.1128/aem.41.3.729-736.1981 (MIBiG attaches this reference to the compound, as support for its STRUCTURE: every compound-level method in the release is structure elucidation (NMR, mass spectrometry, X-ray, total synthesis). It establishes what the molecule is. It is NOT evidence that this organism produces it; MIBiG attaches no reference to the producer link at all.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-14 · codex · LLM-assisted
Added one primary-backed qualified RPB1 laboratory resistance association for named mycophenolic acid. Retained mixed growth responses and IMD probe-specificity limits. Kept the UniProt protein, locus and S288c strain taxonomy reference-only, with no exact experimental allele or genome assigned. No numeric AST, exact variant, construct or protocol was added. Whole-record review remains open.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (mycophenolic acid) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Penicillium brevicompactum)