monodictyphenone

CHEBI:64398 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 member of the class of benzophenones in which one phenyl group is substituted at positions 2 and 6 by hydroxy groups while the other is substituted at positions 2, 4, and 6 by hydroxy, methyl, and carboxy groups, respectively. First obtained from the fungal strain Monodictys putredinis, isolated from the inner tissue of a marine green alga, it was subsequently obtained from the fungus Aspergillus nidulans.

Structure

Standard InChIKey	UMNWQJSVQOCNEM-UHFFFAOYSA-N
SMILES	CC1=CC(C(O)=O)=C(C(=O)C2=C(O)C=CC=C2O)C(O)=C1
Stereochemistry	fully defined
Cross-references	npatlas:NPA016280, pubchem:16114922

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
Aspergillus nidulans FGSC A4 NCBITaxon:227321	BGC_CHARACTERIZED	mibig:BGC0000101	PMID:19448638

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
Monodictys putredinis NCBITaxon:2075174	LOTUS	DOI:10.1021/NP060505O
Monodictys putredinis NCBITaxon:2075174	LOTUS	DOI:10.1021/NP060505O.S001
Monodictys putredinis NCBITaxon:2075174	LOTUS	DOI:10.1021/NP800392W

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000101	Aspergillus nidulans FGSC A4 NCBITaxon:227321	CLUSTER_DEMONSTRATED	genbank:BN001308.1

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 4 nodes, 3 edges

MITE-asserted PhoJ ring-opening step yielding the exact monodictyphenone structure as a reported intermediate in phomoxanthone A biosynthesis. The native Diaporthe SYSU-MS4722 reference is grounded in NCBIProtein, not a UniParc ID relabeled as UniProtKB. This does not assign PhoJ to the owner's distinct Aspergillus/BGC0000101 source or change producer, cluster or occurrence evidence; not full-record sign-off.

Subject	Predicate	Object	Notes	Evidence
PhoJ native reference from Diaporthe SYSU-MS4722	is_database_reported_catalyst_of	MITE-reported PhoJ ring opening	MITE supplies the compound-specific functional assertion; sequence deposits establish identity only. The Diaporthe reference is not inferred to be the owner's Aspergillus nidulans FGSC A4 protein. No rates, assay conditions, active-site residues, cofactor state or physiological complex is claimed; no inaccessible primary data are adopted.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json https://www.ncbi.nlm.nih.gov/protein/UPG58739.1 https://www.ncbi.nlm.nih.gov/nuccore/OL450415.1 https://www.uniprot.org/uniparc/UPI00204975FE reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000158 version 2, active, at the pinned commit. It names PhoJ as a dioxygenase supporting ring opening to monodictyphenone in the phomoxanthone A pathway. Its heterologous-expression code is not personally inspected experimental data; the cited primary paper was inaccessible. Its retired BGC0003093 link was removed by MITE and is not restored here. snippet ring-opening strategy to form monodictyphenone reference https://www.ncbi.nlm.nih.gov/protein/UPG58739.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Complete GenPept and independent coded_by inspected: phoJ, Diaporthe sp. strain SYSU-MS4722, taxon 1756133, 452 residues. The deposited phomoxanthone J product label denotes this gene product, not a chemical identifier. reference https://www.ncbi.nlm.nih.gov/nuccore/OL450415.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-07 notes Genomic DNA deposit with complete exact CDS 1..1359, plus strand, codon_start 1, default translation table 1. Full 1359-nt translation equals the annotation, independent UPG58739.1 and UniParc452aa; coded_by DNA/coordinates match. Gene and mRNA boundaries are fuzzy, so this is not a full transcript/promoter or historical construct/stock claim. reference https://www.uniprot.org/uniparc/UPI00204975FE evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Sequence archive matches all 452 residues and links active EMBL UPG58739 version 1. The inspected record has no UniProtKB cross-reference; the exact taxon/gene query also returned no current entry. No UniProtKB example was selected. The additional WYA90026 archive link is not adopted as an independently checked native deposit.
MITE-encoded ring-opening substrate	is_database_reported_substrate_of	MITE-reported PhoJ ring opening	The node denotes the pinned MITE example substrate. It remains ungrounded; no external compound identifier, complete substrate stereochemistry or additional pathway step is inferred from the encoded ring system.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000158 version 2, active, at the pinned commit. It names PhoJ as a dioxygenase supporting ring opening to monodictyphenone in the phomoxanthone A pathway. Its heterologous-expression code is not personally inspected experimental data; the cited primary paper was inaccessible. Its retired BGC0003093 link was removed by MITE and is not restored here.
MITE-reported PhoJ ring opening	has_database_reported_product	monodictyphenone	Pinned MITE product matches full owner InChIKey UMNWQJSVQOCNEM-UHFFFAOYSA-N and complete stereochemical status using the repository helper and RDKit 2026.03.5. MITE's description places it as a phomoxanthone A intermediate; no downstream transformation or final-product claim is added. The owner's BGC_CHARACTERIZED Aspergillus producer, CLUSTER_DEMONSTRATED BGC0000101/BN001308.1 and separate Monodictys occurrences remain unchanged.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000158.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000158 version 2, active, at the pinned commit. It names PhoJ as a dioxygenase supporting ring opening to monodictyphenone in the phomoxanthone A pathway. Its heterologous-expression code is not personally inspected experimental data; the cited primary paper was inaccessible. Its retired BGC0003093 link was removed by MITE and is not restored here.

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

Causal graph — biosynthesis 4 nodes, 3 edges

Separate MITE-reported PhoL reduction consuming exact monodictyphenone as substrate. Native Diaporthe SYSU-MS4722 PhoL is sequence-grounded in NCBIProtein, not a UniParc accession relabeled as UniProtKB. This context preserves the prior PhoJ graph that forms the owner compound and does not transfer either reference to the distinct imported Aspergillus/BGC0000101 source. Functional evidence is database-level; no primary assay or full-record sign-off is claimed.

Subject	Predicate	Object	Notes	Evidence
PhoL native Diaporthe SYSU-MS4722 reference	is_database_reported_catalyst_of	MITE-reported PhoL net reduction	MITE supplies the compound-specific functional assertion. Its encoded net carboxyl-to-hydroxymethyl change is not an independently inspected purified-enzyme assay or proof of PhoL-alone sufficiency and intervening reaction steps. CDD/UniParc NAD(P)-binding and SDR annotations do not establish a measured cofactor, binding site or occupancy. Native sequence identity is not historical assay-stock or construct identity.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json https://www.ncbi.nlm.nih.gov/protein/UPG58741.1 https://www.ncbi.nlm.nih.gov/nuccore/OL450417.1 https://www.uniprot.org/uniparc/UPI00205DA260 reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000157 version2 names PhoL and GenPeptUPG58741.1; its uniprot field contains the UniParc archive UPI00205DA260, not UniProtKB. Its single reaction example consumes monodictyphenone and encodes a hydroxymethyl product marked intermediate. Heterologous expression is the database evidence code, not an independently inspected assay. The cited DOI10.1021/acs.orglett.2c01050 was inaccessible. MITE removed retired BGC0003093; it is not restored or treated as active here. snippet PhoL is responsible for reduction of monodictyphenone towards the biosynthesis of phomoxanthone A reference https://www.ncbi.nlm.nih.gov/protein/UPG58741.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Independent complete328-aa native PhoL reference, genephoL, Diaporthe sp. SYSU-MS4722/taxon1756133. The deposited product label phomoxanthone L denotes the protein, not a chemical identifier. coded_by joins OL450417.1:1..367 and476..1095. CDD domain/site annotations are not newly inspected biochemical measurements. reference https://www.ncbi.nlm.nih.gov/nuccore/OL450417.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-07 notes Complete987-nt plus two-exon CDS1..367,476..1095, codon1/defaulttable1, equals annotation, independent GenPept and UniParc328aa; independent coded_by DNA/coordinates and SYSU-MS4722/taxon1756133 agree. Complete1198-bp genomic deposit read. CDS boundaries are exact but gene/mRNA boundaries fuzzy; no full transcript/promoter or historical stock/construct claimed. reference https://www.uniprot.org/uniparc/UPI00205DA260 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Archive matches all328residues and contains only activeEMBL UPG58741version1, genephoL/taxon1756133, with no UniProtKB link. Current queries organism_id:1756133 AND gene_exact:phoL and xref:embl-UPG58741 returned no entries on2026-10-07; suggestions were not followed. No UniProtKB example selected in this bounded search, not a global absence claim. UniParc is not a UniProtKB accession.
monodictyphenone	is_database_example_substrate_of	MITE-reported PhoL net reduction	Pinned exact-structure screening matches the MITE substrate to full owner key UMNWQJSVQOCNEM-UHFFFAOYSA-N with complete stereochemistry. This context consumes the owner, whereas its preserved PhoJ graph forms it. No source producer-grade transfer, Monodictys occurrence upgrade or claim that this Diaporthe reference is an Aspergillus nidulans FGSC A4 protein is made.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000157 version2 names PhoL and GenPeptUPG58741.1; its uniprot field contains the UniParc archive UPI00205DA260, not UniProtKB. Its single reaction example consumes monodictyphenone and encodes a hydroxymethyl product marked intermediate. Heterologous expression is the database evidence code, not an independently inspected assay. The cited DOI10.1021/acs.orglett.2c01050 was inaccessible. MITE removed retired BGC0003093; it is not restored or treated as active here.
MITE-reported PhoL net reduction	has_database_example_product	MITE-encoded reduced hydroxymethyl intermediate	The encoded hydroxymethyl product remains externally ungrounded and source-marked intermediate. No exact named product ID, phomoxanthone A final-product claim, downstream sequence or cofactor stoichiometry is inferred. The original PhoJ graph, Aspergillus producer/BGC0000101, occurrence evidence and SEEDED status remain unchanged; retired BGC0003093 is not restored.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000157.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000157 version2 names PhoL and GenPeptUPG58741.1; its uniprot field contains the UniParc archive UPI00205DA260, not UniProtKB. Its single reaction example consumes monodictyphenone and encodes a hydroxymethyl product marked intermediate. Heterologous expression is the database evidence code, not an independently inspected assay. The cited DOI10.1021/acs.orglett.2c01050 was inaccessible. MITE removed retired BGC0003093; it is not restored or treated as active here.

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

Explore across X-Mech

AntibioticMech (monodictyphenone) ↗ MediaIngredientMech (CHEBI:64398) ↗ TaxonMech: Aspergillus nidulans FGSC A4 (NCBITaxon:227321) ↗ PathwayMech (mibig:BGC0000101) ↗

Provenance

Source concept	Source	Version
BGC0000101	MIBIG	5
CHEBI:64398	CHEBI	3-star

This page is generated from data/natural_products/polyketides/monodictyphenone.yaml, which is generated from the committed inventories. Neither is edited by hand.