NaturalProductMech

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notoamide A

naturalproductmech:mibig-edbab72597 MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKeyKGCIBVDLLPYXFL-OFVWMMNVSA-N
SMILESCC1(C)[C@@H]2C[C@]34CCCN3C(=O)[C@@]2(C[C@@]11C(=O)N(O)C2=C1C=CC1=C2C=CC(C)(C)O1)NC4=O
Stereochemistryfully defined
Cross-referencesnpatlas:NPA04681, npatlas:NPA004681

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, terpene, other, pks, from MIBiG.

Producer organisms 3

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.

TaxonBasisClusterEvidence
Aspergillus sp. MF297-2
NCBITaxon:877550		 BGC_CORRELATED mibig:BGC0001084 PMID:20722388
Aspergillus versicolor
NCBITaxon:46472		 SOURCE_ASSERTION mibig:BGC0000818 PMID:23213353
Aspergillus sp. FM242
NCBITaxon:2741095		 SOURCE_ASSERTION mibig:BGC0002254 PMID:32433885

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.

TaxonSourceReference
Aspergillus
NCBITaxon:5052		 LOTUS DOI:10.1002/ANIE.200604381
Aspergillus
NCBITaxon:5052		 LOTUS DOI:10.1021/JA1049302
Aspergillus
NCBITaxon:5052		 LOTUS DOI:10.1021/NP0102758
Aspergillus
NCBITaxon:5052		 LOTUS DOI:10.1021/NP800471Y

Biosynthetic gene clusters 3

AccessionHostLocus evidenceGenome
mibig:BGC0001084 Aspergillus sp. MF297-2
NCBITaxon:877550 		CLUSTER_CORRELATED genbank:HM622670.1
mibig:BGC0000818 Aspergillus versicolor
NCBITaxon:46472 		CLUSTER_UNSTATED genbank:JQ708194.1
mibig:BGC0002254 Aspergillus sp. FM242
NCBITaxon:2741095 		CLUSTER_UNSTATED genbank:MT457561.1

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

PRODUCERS & OCCURRENCE 3 producers (0 causal) 4 cited occurrences BIOSYNTHETIC LOCUS 3 gene clusters 0 curated pathway steps NATURAL PRODUCT notoamide A naturalproductmech:mibig-edbab72597 Unclassified TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 6 graphs

Causal graph — biosynthesis 2 nodes, 1 edge

Native identity in the MF297-2/BGC0001084 context only. The spliced genomic reference is not a verified experimental transcript or tagged construct, and is not transferred to the distinct BGC0000818 or BGC0002254 source clusters.

SubjectPredicateObjectNotesEvidence
notF CDS (HM622670.1, two reverse-strand exons) encodes the native protein reference NotF (MF297-2 native reference) Aspergillus sp. MF297-2, taxon 877550; complement(join(17924..18053,18126..19354)); 452 amino acids.
https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
https://www.ncbi.nlm.nih.gov/nuccore/GU564535.1
https://www.uniprot.org/uniprotkb/E0Y3X1/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
    evidence type
    DATABASE_ASSERTION
    notes
    GenBank links this two-exon CDS to ADM34139.1 and names NotF; the CDS lacks a gene-name qualifier.
    retrieved on
    2026-10-08
    snippet
    /note="NotF"
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/GU564535.1
    evidence type
    DATABASE_ASSERTION
    notes
    The separate notF gene deposit has CDS join(1..1229,1302..1431) and protein ADM34132.1 in the same strain.
    retrieved on
    2026-10-08
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X1/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Reviewed entry version 40, sequence version 1. CDS-aware translations of both deposits, both deposited translations, both independent GenPept proteins and E0Y3X1 match over all 452 residues. This establishes native reference identity, not the sequence of an experimental construct.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 4 nodes, 3 edges

Partial early-intermediate graph in the MF297-2 notoamide pathway context annotated by UniProt. NotF does not directly make notoamide A. No downstream reactions or final hydroxylase are asserted. The original paper DOI:10.1021/ja1049302 is cited by the database but its full text was not inspected; the 2020 specificity study was read at abstract level only. Assembly, kinetics and strict substrate exclusivity are not asserted.

SubjectPredicateObjectNotesEvidence
NotF (MF297-2 native reference) is annotated to catalyze NotF early reverse C2-prenylation Native reference, not a sequence-verified assay construct. The reaction uses dimethylallyl diphosphate as prenyl donor and releases diphosphate. Formation of the later bicyclic core is not asserted.
https://www.uniprot.org/uniprotkb/E0Y3X1/entry
DOI:10.1007/s00203-020-01854-7
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X1/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Entry version 40 annotates EC:2.5.1.109 and RHEA:35943, with physiological left-to-right RHEA:35944, citing PMID:20722388.
    retrieved on
    2026-10-08
    snippet
    brevianamide F + dimethylallyl diphosphate = deoxybrevianamide E + diphosphate
  • reference
    DOI:10.1007/s00203-020-01854-7
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract only: NotF from MF297-2 catalyzes reverse C2-prenylation of brevianamide F; comparison of 14 cyclodipeptides by MS qualifies the earlier exclusive-substrate claim. No individual analogue product structures or kinetic values are imported.
    retrieved on
    2026-10-08
    snippet
    NotF and BrePT share similar catalytic ability and substrate promiscuity.
brevianamide F is the annotated substrate of NotF early reverse C2-prenylation The cyclic L-Trp/L-Pro substrate, not an unspecified stereoisomer.
https://www.uniprot.org/uniprotkb/E0Y3X1/entry
https://www.ebi.ac.uk/chebi/CHEBI:64530
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X1/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Catalytic activity assigns brevianamide F as the prenyl acceptor.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:64530
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies brevianamide F with full InChIKey RYFZBPVMVYTEKZ-KBPBESRZSA-N and the 3S,8aS stereochemistry.
    retrieved on
    2026-10-08
NotF early reverse C2-prenylation has the annotated product deoxybrevianamide E An early intermediate, not notoamide A. This edge does not prove an experimentally complete route from the intermediate to this owner.
https://www.uniprot.org/uniprotkb/E0Y3X1/entry
https://www.ebi.ac.uk/chebi/CHEBI:72948
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X1/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Catalytic activity identifies deoxybrevianamide E; the broad pathway annotation leaves the final hydroxylation enzyme leading to notoamide A unidentified.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:72948
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies the reverse C2-prenylated product with full InChIKey KUGNSEAHJVSMAJ-IRXDYDNUSA-N.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 2 nodes, 1 edge

Native identity in the MF297-2/BGC0001084 context only. The spliced genomic reference is not a verified experimental transcript or assay construct, and is not transferred to the distinct BGC0000818 or BGC0002254 source clusters.

SubjectPredicateObjectNotesEvidence
notC CDS (HM622670.1, two forward-strand exons) encodes the native protein reference NotC (MF297-2 native reference) Aspergillus sp. MF297-2, taxon 877550; join(5819..6996,7066..7168); 426 amino acids.
https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
https://www.ncbi.nlm.nih.gov/nuccore/GU564534.1
https://www.uniprot.org/uniprotkb/E0Y3X0/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
    evidence type
    DATABASE_ASSERTION
    notes
    GenBank links this two-exon CDS to ADM34136.1 and names NotC; the CDS lacks a gene-name qualifier.
    retrieved on
    2026-10-08
    snippet
    /note="NotC"
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/GU564534.1
    evidence type
    DATABASE_ASSERTION
    notes
    The separate notC gene deposit has CDS join(1..1178,1248..1350) and protein ADM34131.1 in the same strain.
    retrieved on
    2026-10-08
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X0/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Reviewed entry version 39, sequence version 1. CDS-aware translations of both deposits, both deposited translations, both independent GenPept proteins and E0Y3X0 match over all 426 residues. This establishes native reference identity, not the sequence of an experimental construct.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 4 nodes, 3 edges

Partial intermediate graph in the MF297-2 notoamide pathway context annotated by UniProt. NotC does not directly make notoamide A. No verified hydroxylation bridge from the existing NotF product to the NotC substrate, downstream route or final hydroxylase is asserted. DOI:10.1021/ja1049302 is cited by the database; its primary contents were not inspected. Assembly, kinetics and strict substrate exclusivity are not asserted.

SubjectPredicateObjectNotesEvidence
NotC (MF297-2 native reference) is annotated to catalyze NotC normal C7-prenylation Native reference, not a sequence-verified assay construct. Normal prenylation at C7, distinct from NotF reverse C2-prenylation; dimethylallyl diphosphate is the donor and diphosphate is released.
https://www.uniprot.org/uniprotkb/E0Y3X0/entry
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X0/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Entry version 39 annotates RHEA:62344 and physiological left-to-right RHEA:62345, citing PMID:20722388. This is database evidence, not an independently inspected experiment.
    retrieved on
    2026-10-08
    snippet
    6-hydroxydeoxybrevianamide E + dimethylallyl diphosphate = notoamide S + diphosphate
6-hydroxydeoxybrevianamide E is the annotated substrate of NotC normal C7-prenylation The hydroxylated intermediate, not the unhydroxylated NotF product.
https://www.uniprot.org/uniprotkb/E0Y3X0/entry
https://www.ebi.ac.uk/chebi/CHEBI:145682
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X0/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Catalytic activity assigns 6-hydroxydeoxybrevianamide E as the prenyl acceptor; no strict substrate-exclusivity claim is adopted.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:145682
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies this stereochemically specified intermediate with full InChIKey DHOZDQLRUFUUQZ-IRXDYDNUSA-N.
    retrieved on
    2026-10-08
NotC normal C7-prenylation has the annotated product notoamide S Notoamide S is an intermediate, not notoamide A. This edge does not prove an experimentally complete route to the owner structure.
https://www.uniprot.org/uniprotkb/E0Y3X0/entry
https://www.ebi.ac.uk/chebi/CHEBI:145683
  • reference
    https://www.uniprot.org/uniprotkb/E0Y3X0/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Catalytic activity identifies notoamide S. The broader pathway annotation contains proposed downstream assignments and leaves the final hydroxylation enzyme leading to notoamide A unidentified.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:145683
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies notoamide S with full InChIKey ZGWIWQJHQKPWGB-PMACEKPBSA-N.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 2 nodes, 1 edge

Native full-length reference identity in MF297-2/BGC0001084 only. The spliced genomic reference is not a verified experimental transcript or assay construct. Predicted signal cleavage, membrane topology and glycosylation are not experimentally verified here. No transfer to BGC0000818 or BGC0002254.

SubjectPredicateObjectNotesEvidence
notG CDS (HM622670.1, five reverse-strand exons) encodes the full-length native protein reference NotG (MF297-2 full-length native reference) Aspergillus sp. MF297-2, taxon 877550; complement(join(19899..20086,20171..20272,20337..20635,20689..20810,20879..21799)); 543 amino acids.
https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
https://www.ncbi.nlm.nih.gov/protein/ADM34140.1
https://www.uniprot.org/uniprotkb/E1ACQ2/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/HM622670.1
    evidence type
    DATABASE_ASSERTION
    notes
    GenBank links the five-exon CDS to ADM34140.1 and names NotG; the CDS lacks a gene-name qualifier.
    retrieved on
    2026-10-08
    snippet
    /note="NotG"
  • reference
    https://www.ncbi.nlm.nih.gov/protein/ADM34140.1
    evidence type
    DATABASE_ASSERTION
    notes
    The separate GenPept record names NotG and maps its 543-residue reference to the same reverse-strand spliced CDS.
    retrieved on
    2026-10-08
  • reference
    https://www.uniprot.org/uniprotkb/E1ACQ2/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Reviewed entry version 39, sequence version 1. CDS-aware translation of HM622670.1, its deposited translation, GenPept ADM34140.1 and E1ACQ2 match over all 543 residues. This establishes full-length reference identity, not experimental mature processing or reaction verification.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 4 nodes, 3 edges

Partial, explicitly inferred intermediate graph: UniProt proposes NotG for C6-hydroxylation between the annotated NotF product and NotC substrate. This is a hypothesis, not a demonstrated bridge between those graphs or a complete route to notoamide A. The database-cited DOI:10.1021/ja1049302 and DOI:10.1039/C2MD20029E primary contents were not inspected. No final hydroxylase, assembly, native heme occupancy or kinetic claim is asserted.

SubjectPredicateObjectNotesEvidence
NotG (MF297-2 full-length native reference) is proposed to catalyze Proposed NotG C6-hydroxylation Database-inferred assignment, not a directly demonstrated NotG reaction. The reaction node is ungrounded: no Rhea or complete EC identifier was verified for this proposed transformation.
https://www.uniprot.org/uniprotkb/E1ACQ2/entry
  • reference
    https://www.uniprot.org/uniprotkb/E1ACQ2/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Entry version 39 marks this NotG-specific function Probable. The experimental citations attached to its broader pathway paragraph are not evidence that this individual step was demonstrated. No CATALYTIC ACTIVITY comment is present.
    retrieved on
    2026-10-08
    snippet
    likely catalyzed by the cytochrome P450 monooxygenase notG, to yield 6-hydroxy-deoxybrevianamide E (Probable)
deoxybrevianamide E is the proposed substrate of Proposed NotG C6-hydroxylation Proposed substrate identity, not an assayed NotG substrate-specificity result.
https://www.uniprot.org/uniprotkb/E1ACQ2/entry
https://www.ebi.ac.uk/chebi/CHEBI:72948
  • reference
    https://www.uniprot.org/uniprotkb/E1ACQ2/entry
    evidence type
    DATABASE_ASSERTION
    notes
    The Probable function clause proposes C6 hydroxylation of deoxybrevianamide E; it does not establish a verified NotG assay.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:72948
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies deoxybrevianamide E with full InChIKey KUGNSEAHJVSMAJ-IRXDYDNUSA-N. Molecular identity does not prove participation in the proposed reaction.
    retrieved on
    2026-10-08
Proposed NotG C6-hydroxylation has the proposed product 6-hydroxydeoxybrevianamide E Proposed hydroxylated intermediate, not notoamide A. No complete downstream route or experimentally verified NotF-to-NotC bridge.
https://www.uniprot.org/uniprotkb/E1ACQ2/entry
https://www.ebi.ac.uk/chebi/CHEBI:145682
  • reference
    https://www.uniprot.org/uniprotkb/E1ACQ2/entry
    evidence type
    DATABASE_ASSERTION
    notes
    The Probable function clause names 6-hydroxy-deoxybrevianamide E as the proposed product; the final hydroxylation leading to notoamide A remains unidentified in the broader annotation.
    retrieved on
    2026-10-08
  • reference
    https://www.ebi.ac.uk/chebi/CHEBI:145682
    evidence type
    DATABASE_ASSERTION
    notes
    ChEBI identifies 6-hydroxydeoxybrevianamide E with full InChIKey DHOZDQLRUFUUQZ-IRXDYDNUSA-N. This is chemical-identity evidence only, not proof of the NotG assignment.
    retrieved on
    2026-10-08

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

Explore across X-Mech

AntibioticMech (notoamide A) ↗ MediaIngredientMech (naturalproductmech:mibig-edbab72597) ↗ TaxonMech: Aspergillus sp. MF297-2 (NCBITaxon:877550) ↗ TaxonMech: Aspergillus versicolor (NCBITaxon:46472) ↗ TaxonMech: Aspergillus sp. FM242 (NCBITaxon:2741095) ↗ PathwayMech (mibig:BGC0001084) ↗ PathwayMech (mibig:BGC0000818) ↗ PathwayMech (mibig:BGC0002254) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0000818, BGC0001084, BGC0002254. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source conceptSourceVersion
BGC0001084MIBIG5
BGC0000818MIBIG5
BGC0002254MIBIG3

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