terrequinone A

CHEBI:64534 EXACT SEEDED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

A bisindole alkaloid that is quinone bearing a hydroxy substituent at position 2, a 3,3-dimethylallyl group at position 5 and two indol-3-yl groups at positions 3 and 6, one of which is carrying a 1,1-dimethylallyl group at position 2.

Structure

Standard InChIKey	HBMHEGGZNWXZRA-UHFFFAOYSA-N
SMILES	CC(C)=CCC1=C(C2=CNC3=C2C=CC=C3)C(=O)C(O)=C(C2=C(NC3=C2C=CC=C3)C(C)(C)C=C)C1=O
Stereochemistry	fully defined
Cross-references	npatlas:NPA05272

Filing pathway

Alkaloids — 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, 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 nidulans FGSC A4 NCBITaxon:227321	BGC_CHARACTERIZED	mibig:BGC0000442	PMID:16426969

Occurrences 2

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 terreus NCBITaxon:33178	LOTUS	DOI:10.1021/NP040139D
Aspergillus NCBITaxon:5052	LOTUS	DOI:10.1021/NP040139D

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000442	Aspergillus nidulans FGSC A4 NCBITaxon:227321	CLUSTER_DEMONSTRATED	genbank:BN001305.1

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 7 nodes, 6 edges

TdiA-TdiE canonical references in terrequinone A biosynthesis. Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade.

Subject	Predicate	Object	Notes	Evidence
tdiA (canonical reference)	is_database_supported_participant_in	terrequinone A biosynthetic process	Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade. The MIBiG-derived GenBank translation CBF80711.1 has 949 residues and differs from this 970-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence.	https://www.uniprot.org/uniprotkb/A7XRY0 https://www.ebi.ac.uk/ena/browser/view/EF550581.1 reference https://www.uniprot.org/uniprotkb/A7XRY0 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Swiss-Prot entry 83, sequence 1, 970 residues; protein existence 1: Evidence at protein level. UniProt assigns taxon 227321, Aspergillus nidulans FGSC A4 (also named Emericella nidulans). Its FUNCTION comment names terrequinone A biosynthesis, and its GO:1900796 annotation is IMP:AspGD, citing PMID:17704773; this remains a database assertion, not independent primary-assay review. The mRNA reference is linked to DOI:10.1038/nchembio.2007.20 in UniProt. That paper was available only as a subscription preview; methods, figures and supplements were not inspected. The distinct 2023 engineered-host paper PMC9979454 presented a browser challenge; its constructs are not transferred here. The MIBiG-derived GenBank translation CBF80711.1 has 949 residues and differs from this 970-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence. snippet part of the gene cluster that mediates the biosynthesis of terrequinone A reference https://www.ebi.ac.uk/ena/browser/view/EF550581.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Complete mRNA CDS 1..2913, ATG start, TAG stop, codon_start 1, standard translation table 1. Translation equals deposited ABU51602.1 and all 970 canonical A7XRY0 residues. The ENA source qualifier is Aspergillus nidulans, taxon 162425, without an explicit strain; FGSC A4/taxon 227321 comes from UniProt, not this qualifier. The deposit cites PMID:17704773 and DOI:10.1038/nchembio.2007.20. This is reference-sequence correspondence only, not proof of assay tags, engineered substitutions, recombinant processing or exact experimental stock. No full native-genome reconstruction or current RefSeq audit is claimed.
tdiB (canonical reference)	is_database_supported_participant_in	terrequinone A biosynthetic process	Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade. The MIBiG-derived GenBank translation CBF80712.1 is identical to the canonical reference; this does not establish historical assay-stock identity.	https://www.uniprot.org/uniprotkb/A7XRY3 https://www.ebi.ac.uk/ena/browser/view/EF550582.1 reference https://www.uniprot.org/uniprotkb/A7XRY3 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Swiss-Prot entry 55, sequence 1, 419 residues; protein existence 1: Evidence at protein level. UniProt assigns taxon 227321, Aspergillus nidulans FGSC A4 (also named Emericella nidulans). Its FUNCTION comment names terrequinone A biosynthesis, and its GO:1900796 annotation is IDA:AspGD, citing PMID:17704773; this remains a database assertion, not independent primary-assay review. The mRNA reference is linked to DOI:10.1038/nchembio.2007.20 in UniProt. That paper was available only as a subscription preview; methods, figures and supplements were not inspected. The distinct 2023 engineered-host paper PMC9979454 presented a browser challenge; its constructs are not transferred here. The MIBiG-derived GenBank translation CBF80712.1 is identical to the canonical reference; this does not establish historical assay-stock identity. snippet part of the gene cluster that mediates the biosynthesis of terrequinone A reference https://www.ebi.ac.uk/ena/browser/view/EF550582.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Complete mRNA CDS 1..1260, ATG start, TAG stop, codon_start 1, standard translation table 1. Translation equals deposited ABU51603.1 and all 419 canonical A7XRY3 residues. The ENA source qualifier is Aspergillus nidulans, taxon 162425, without an explicit strain; FGSC A4/taxon 227321 comes from UniProt, not this qualifier. The deposit cites PMID:17704773 and DOI:10.1038/nchembio.2007.20. This is reference-sequence correspondence only, not proof of assay tags, engineered substitutions, recombinant processing or exact experimental stock. No full native-genome reconstruction or current RefSeq audit is claimed.
tdiC (canonical reference)	is_database_supported_participant_in	terrequinone A biosynthetic process	Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade. The MIBiG-derived GenBank translation CBF80714.1 is identical to the canonical reference; this does not establish historical assay-stock identity. The UniProt recommended name specifies probable NADPH dependence, the deposited transcript note says NAD(P)H, and the 2007 abstract says NADH. No cofactor preference is resolved or asserted here.	https://www.uniprot.org/uniprotkb/A7XRY6 https://www.ebi.ac.uk/ena/browser/view/EF550583.1 reference https://www.uniprot.org/uniprotkb/A7XRY6 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Swiss-Prot entry 62, sequence 1, 355 residues; protein existence 2: Evidence at transcript level. UniProt assigns taxon 227321, Aspergillus nidulans FGSC A4 (also named Emericella nidulans). Its FUNCTION comment names terrequinone A biosynthesis, and its GO:1900796 annotation is IMP:UniProt, citing PMID:17704773; this remains a database assertion, not independent primary-assay review. The mRNA reference is linked to DOI:10.1038/nchembio.2007.20 in UniProt. That paper was available only as a subscription preview; methods, figures and supplements were not inspected. The distinct 2023 engineered-host paper PMC9979454 presented a browser challenge; its constructs are not transferred here. The MIBiG-derived GenBank translation CBF80714.1 is identical to the canonical reference; this does not establish historical assay-stock identity. The UniProt recommended name specifies probable NADPH dependence, the deposited transcript note says NAD(P)H, and the 2007 abstract says NADH. No cofactor preference is resolved or asserted here. snippet part of the gene cluster that mediates the biosynthesis of terrequinone A reference https://www.ebi.ac.uk/ena/browser/view/EF550583.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Complete mRNA CDS 1..1068, ATG start, TGA stop, codon_start 1, standard translation table 1. Translation equals deposited ABU51604.1 and all 355 canonical A7XRY6 residues. The ENA source qualifier is Aspergillus nidulans, taxon 162425, without an explicit strain; FGSC A4/taxon 227321 comes from UniProt, not this qualifier. The deposit cites PMID:17704773 and DOI:10.1038/nchembio.2007.20. This is reference-sequence correspondence only, not proof of assay tags, engineered substitutions, recombinant processing or exact experimental stock. No full native-genome reconstruction or current RefSeq audit is claimed.
tdiD (canonical reference)	is_database_supported_participant_in	terrequinone A biosynthetic process	Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade. The MIBiG-derived GenBank translation CBF80716.1 has 444 residues and differs from this 436-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence.	https://www.uniprot.org/uniprotkb/A7XRY8 https://www.ebi.ac.uk/ena/browser/view/EF550584.1 reference https://www.uniprot.org/uniprotkb/A7XRY8 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Swiss-Prot entry 77, sequence 1, 436 residues; protein existence 1: Evidence at protein level. UniProt assigns taxon 227321, Aspergillus nidulans FGSC A4 (also named Emericella nidulans). Its FUNCTION comment names terrequinone A biosynthesis, and its GO:1900796 annotation is IMP:GO_Central, citing PMID:17704773; this remains a database assertion, not independent primary-assay review. The mRNA reference is linked to DOI:10.1038/nchembio.2007.20 in UniProt. That paper was available only as a subscription preview; methods, figures and supplements were not inspected. The distinct 2023 engineered-host paper PMC9979454 presented a browser challenge; its constructs are not transferred here. The MIBiG-derived GenBank translation CBF80716.1 has 444 residues and differs from this 436-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence. snippet part of the gene cluster that mediates the biosynthesis of terrequinone A reference https://www.ebi.ac.uk/ena/browser/view/EF550584.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Complete mRNA CDS 1..1311, ATG start, TAA stop, codon_start 1, standard translation table 1. Translation equals deposited ABU51605.1 and all 436 canonical A7XRY8 residues. The ENA source qualifier is Aspergillus nidulans, taxon 162425, without an explicit strain; FGSC A4/taxon 227321 comes from UniProt, not this qualifier. The deposit cites PMID:17704773 and DOI:10.1038/nchembio.2007.20. This is reference-sequence correspondence only, not proof of assay tags, engineered substitutions, recombinant processing or exact experimental stock. No full native-genome reconstruction or current RefSeq audit is claimed.
tdiE (canonical reference)	is_database_supported_participant_in	terrequinone A biosynthetic process	Canonical reference proteins, not independently inspected assay constructs. This graph adopts database-supported process participation, not reaction order, substrate specificity, catalytic stoichiometry, direct physical interactions, an obligate complex or a complete pathway. GROUNDED denotes identifier identity, not experimental verification by this curation. No producer, BGC, taxonomy, biosynthesis-origin or record-status upgrade. The MIBiG-derived GenBank translation CBF80718.1 has 296 residues and differs from this 317-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence. UniProt calls this a probable methyltransferase and also carries an alternative protein-D label; the tdiE gene name and EF550585.1/ABU51606.1 sequence determine the reference here. No methyltransferase activity, chaperone mechanism or TdiD identity is adopted.	https://www.uniprot.org/uniprotkb/A7XRZ1 https://www.ebi.ac.uk/ena/browser/view/EF550585.1 reference https://www.uniprot.org/uniprotkb/A7XRZ1 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Swiss-Prot entry 50, sequence 1, 317 residues; protein existence 2: Evidence at transcript level. UniProt assigns taxon 227321, Aspergillus nidulans FGSC A4 (also named Emericella nidulans). Its FUNCTION comment names terrequinone A biosynthesis, and its GO:1900796 annotation is IMP:GO_Central, citing PMID:17291795; this remains a database assertion, not independent primary-assay review. The mRNA reference is linked to DOI:10.1038/nchembio.2007.20 in UniProt. That paper was available only as a subscription preview; methods, figures and supplements were not inspected. The distinct 2023 engineered-host paper PMC9979454 presented a browser challenge; its constructs are not transferred here. The MIBiG-derived GenBank translation CBF80718.1 has 296 residues and differs from this 317-residue reference; UniProt flags that genome model as erroneous. It is not treated as the same sequence. UniProt calls this a probable methyltransferase and also carries an alternative protein-D label; the tdiE gene name and EF550585.1/ABU51606.1 sequence determine the reference here. No methyltransferase activity, chaperone mechanism or TdiD identity is adopted. snippet part of the gene cluster that mediates the biosynthesis of terrequinone A reference https://www.ebi.ac.uk/ena/browser/view/EF550585.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Complete mRNA CDS 1..954, ATG start, TGA stop, codon_start 1, standard translation table 1. Translation equals deposited ABU51606.1 and all 317 canonical A7XRZ1 residues. The ENA source qualifier is Aspergillus nidulans, taxon 162425, without an explicit strain; FGSC A4/taxon 227321 comes from UniProt, not this qualifier. The deposit cites PMID:17704773 and DOI:10.1038/nchembio.2007.20. This is reference-sequence correspondence only, not proof of assay tags, engineered substitutions, recombinant processing or exact experimental stock. No full native-genome reconstruction or current RefSeq audit is claimed.
terrequinone A biosynthetic process	has_ontology_defined_primary_output	terrequinone A	GO process identity, not a direct enzyme-to-product reaction or a measurement.	http://purl.obolibrary.org/obo/GO_1900796 https://www.ebi.ac.uk/chebi/CHEBI:64534 https://mibig.secondarymetabolites.org/repository/BGC0000442.5/index.html reference http://purl.obolibrary.org/obo/GO_1900796 evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Existing local OAK GO cache inspected 2026-10-10, not a fresh ontology download. GO:1900796 has the RO:0004008 (has primary output) restriction to CHEBI:64534. The process is not being substituted for a single catalytic reaction. snippet The chemical reactions and pathways resulting in the formation of terrequinone A. reference https://www.ebi.ac.uk/chebi/CHEBI:64534 evidence type CURATOR_INFERENCE retrieved on 2026-10-10 notes Existing local OAK ChEBI cache inspected 2026-10-10, not a fresh source download. Pinned RDKit 2026.03.5 maps the owner MIBiG SMILES, owner InChI and cached ChEBI InChI to HBMHEGGZNWXZRA-UHFFFAOYSA-N, C32H30N2O3, formal charge 0 and no tetrahedral stereocenters. The cached ChEBI SMILES (also in the committed ChEBI inventory) cannot be kekulized by this RDKit version and is explicitly excluded from the equality assertion; it was not silently repaired. The owner uses the valid MIBiG SMILES. This identity check is not an assay-product determination. reference https://mibig.secondarymetabolites.org/repository/BGC0000442.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-10-10 notes Version 5 is active, quality questionable, completeness complete, and lists one compound with exactly the owner SMILES and formula. Its biosynthesis module names CBF80711.1, the 949-residue TdiA model flagged by UniProt; the activity-assay annotation is not transferred to the distinct 970-residue canonical sequence. No antiSMASH neighborhood inference is used. Existing source-owned producer and BGC evidence is unchanged.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Explore across X-Mech

AntibioticMech (terrequinone A) ↗ MediaIngredientMech (CHEBI:64534) ↗ TaxonMech: Aspergillus nidulans FGSC A4 (NCBITaxon:227321) ↗ PathwayMech (mibig:BGC0000442) ↗

Provenance

Source concept	Source	Version
BGC0000442	MIBIG	5
CHEBI:64534	CHEBI	3-star

This page is generated from data/natural_products/alkaloids/terrequinone-a.yaml, which is generated from the committed inventories. Neither is edited by hand.