(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
CHEBI:22450 EXACT SEEDED enzyme inhibitor
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.
Structure
| Standard InChIKey | SZINUGQCTHLQAZ-DQYPLSBCSA-N |
|---|---|
| SMILES | CC(=O)C1=C([C@@H]2[C@@H]3[C@@H](CC4=C5C3=CNC5=CC=C4)C(N2C1=O)(C)C)O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA015449, pubchem:54682463 |
Filing pathway
Unclassified — 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 nrps, 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 |
|---|---|---|---|
| Aspergillus oryzae NCBITaxon:5062 |
SOURCE_ASSERTION | mibig:BGC0000977 | DOI:10.1002/cbic.201000672 |
Occurrences 4
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 aurantiogriseum NCBITaxon:36655 |
LOTUS | DOI:10.1016/0040-4020(68)88113-X |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1002/CBIC.201000672 |
| Penicillium cyclopium NCBITaxon:60167 |
LOTUS | DOI:10.1016/0040-4020(68)88113-X |
| Penicillium vinaceum NCBITaxon:69790 |
LOTUS | DOI:10.1016/J.PHYTOL.2015.05.014 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000977 | Aspergillus oryzae NCBITaxon:5062 |
CLUSTER_UNSTATED | genbank:AB506492.1 |
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
Causal graph — biosynthesis 8 nodes, 10 edges
Six NBRC 4177 reference proteins; only CpaS/CpaA, CpaD and CpaO have database-supported participation edges. CpaR/T/M are encoding context only. Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. MIBiG entry version 4 is active but quality questionable, completeness unknown. Entry version is not a database release version. Its locus has no evidence entries. Source producer/BGC assertion grades remain unchanged. Primary methods, figures, supplements and constructs were not independently inspected. PMID:21608094 was accessible as an abstract/publisher landing only; its UniProt annotations are adopted as database assertions, not independently verified experiments. Other CPA primary leads were inaccessible, rate-limited or browser-challenged. No new biochemical assay claim is imported.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| BGC0000977 (NBRC 4177 reference) | is_database_linked_to_structure | (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one | MIBiG entry version 4 is active but quality questionable, completeness unknown. Entry version is not a database release version. Its locus has no evidence entries. Source producer/BGC assertion grades remain unchanged. This graph retains the exact source-matched neutral owner representation, formula C20H20N2O3, charge zero. Its stored SMILES and InChI parse and agree within this owner under RDKit 2026.03.5. CHEBI:17734 and CHEBI:22450 remain separate hydroxyethylidene and acetyl-enol representations with different Standard InChIKeys; no microstate equivalence or owner merge is inferred. Charged Rhea participants CHEBI:58067/58256 are not substituted. The local ChEBI SMILES parse defect tracked in issue 777 is not used to repair or replace the owner chemistry. Existing CpaH and SERCA content is outside this graph; issue 147 remains unresolved. Exact owner CHEBI:22450, Standard InChIKey SZINUGQCTHLQAZ-DQYPLSBCSA-N. | https://mibig.secondarymetabolites.org/repository/BGC0000977.4/annotations.json |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | CpaS/CpaA (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. cpaA is also called CpaS. This is the complete 3907-residue canonical reference, not a selected assay construct or demonstrated domain-by-domain mechanism. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
| CpaS/CpaA (NBRC 4177 reference) | is_database_supported_biosynthetic_participant_for | (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. cpaA is also called CpaS. This is the complete 3907-residue canonical reference, not a selected assay construct or demonstrated domain-by-domain mechanism. Primary methods, figures, supplements and constructs were not independently inspected. PMID:21608094 was accessible as an abstract/publisher landing only; its UniProt annotations are adopted as database assertions, not independently verified experiments. Other CPA primary leads were inaccessible, rate-limited or browser-challenged. No new biochemical assay claim is imported. | https://www.uniprot.org/uniprotkb/B6F209 |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | cpaD (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. The complete 437-residue canonical reference is selected; no exact prenylation reaction or substrate specificity is adopted. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
| cpaD (NBRC 4177 reference) | is_database_supported_biosynthetic_participant_for | (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. The complete 437-residue canonical reference is selected; no exact prenylation reaction or substrate specificity is adopted. Primary methods, figures, supplements and constructs were not independently inspected. PMID:21608094 was accessible as an abstract/publisher landing only; its UniProt annotations are adopted as database assertions, not independently verified experiments. Other CPA primary leads were inaccessible, rate-limited or browser-challenged. No new biochemical assay claim is imported. | https://www.uniprot.org/uniprotkb/F5HN73 |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | cpaO (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. The 455-residue canonical precursor is selected. UniProt predicts signal residues 1..25 and chain 26..455; no mature construct is adopted. Its FAD annotation is by similarity to B8NI10, not a new exact-protein cofactor experiment. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
| cpaO (NBRC 4177 reference) | is_database_supported_biosynthetic_participant_for | (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. The 455-residue canonical precursor is selected. UniProt predicts signal residues 1..25 and chain 26..455; no mature construct is adopted. Its FAD annotation is by similarity to B8NI10, not a new exact-protein cofactor experiment. Primary methods, figures, supplements and constructs were not independently inspected. PMID:21608094 was accessible as an abstract/publisher landing only; its UniProt annotations are adopted as database assertions, not independently verified experiments. Other CPA primary leads were inaccessible, rate-limited or browser-challenged. No new biochemical assay claim is imported. | https://www.uniprot.org/uniprotkb/F5HN72 |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | cpaR (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. Protein existence is inferred from homology. Encoding context does not establish a required regulatory role. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | cpaT (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. Protein existence is inferred from homology. Encoding context does not establish a required transport or biosynthetic role. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
| BGC0000977 (NBRC 4177 reference) | contains_cds_encoding_reference | cpaM (NBRC 4177 reference) | Reference-sequence identity and cluster encoding context are distinct from function. GROUNDED denotes identifier identity, not experimental validation. No exact reaction, ordered pathway, substrate specificity, stoichiometry, physical complex, mature processing or assayed construct is asserted. References from NBRC 4177, CA28, RIB40 and NRRL 3357 are not interchangeable. Protein existence is inferred from homology. The native product is hypothetical; UniProt calls it a putative methyltransferase and reports no apparent involvement in CPA/2-oxo-CPA biosynthesis. No methylation or required biosynthetic role is asserted. | https://www.ebi.ac.uk/ena/browser/view/AB506492.1 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 10
Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.
| Assay | Result | Target enzyme | Source detail |
|---|---|---|---|
| Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB | KI 0.12 uM; ACTIVE | Not recorded | PMID:17259168
|
| Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB | KI 0.12 uM; ACTIVE | Not recorded | PMID:17259168
|
| Experimentally measured binding affinity data derived from PDB | ACTIVE | Not recorded | PMID:17259168
|
| Experimentally measured binding affinity data derived from PDB | ACTIVE | Not recorded | PMID:17259168
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:P11086 | PMID:36976909
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:P21964 | PMID:36976909
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:P40261 | PMID:36976909
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:P50135 | PMID:36976909
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:Q14353 | PMID:36976909
|
| Primary Screen for Target Class Profiling of Small Molecule Inhibitors of Methyltransferases | ACTIVE | UniProtKB:Q14749 | PMID:36976909
|
Explore across X-Mech
AntibioticMech ((6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one) ↗
MediaIngredientMech (CHEBI:22450) ↗
TaxonMech: Aspergillus oryzae (NCBITaxon:5062) ↗
PathwayMech (mibig:BGC0000977) ↗
Open questions 1
name-disagreement — ChEBI calls this structure "(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one" and MIBiG calls it 'cyclopiazonic acid'. 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 |
|---|---|---|
| BGC0000977 | MIBIG | 4 |
| CHEBI:22450 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/6ar-11as-11br-10-acetyl-11-hydroxy-7-7-dimethyl-2-6-6a-7-11a-11b-hexahydro-9h-py.yaml, which is generated from the committed inventories. Neither is edited by hand.