jamaicamide A

naturalproductmech:mibig-0ce6527209 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKey	NAIKIJSSBJHCBL-IPUGVWFUSA-N
SMILES	CO\C(CCNC(=O)CC\C=C\C(C)CC\C(CCCC#CBr)=C\Cl)=C\C(=O)N1C(C)C=CC1=O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	npatlas:NPA013036, cyanometdb:CyanoMetDB_1360

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
Lyngbya majuscula NCBITaxon:158786	SOURCE_ASSERTION	mibig:BGC0001001	DOI:10.1016/j.chembiol.2004.03.030

Occurrences 1

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
Lyngbya majuscula NCBITaxon:158786	LOTUS	DOI:10.1016/J.CHEMBIOL.2004.03.030

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001001	Lyngbya majuscula NCBITaxon:158786	CLUSTER_UNSTATED	genbank:AY522504.1

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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

#	Enzyme	Reaction	Substrate → product	Evidence
1	JamD flavin-dependent halogenase (MITE annotation) UniProtKB:Q6E7K6		ungrounded → ungrounded	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json

Entry 1: MITE assigns JamD to jamaicamide B-to-A bromination. Its literal B and A models have the respective owners' connectivity, formula and charge but omit all three alkene configurations retained by those owners. Both models and owners leave two tetrahedral centers unspecified. This is missing stereochemistry, not a demonstrated stereochemical conflict or an exact full-InChIKey join. The models remain separate from the grounded record. Primary assays and constructs were not inspected, so the pathway entry remains proposed; no exact chemical conversion of the owner, balanced reaction, physiological order or native production experiment is asserted.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Partial Lyngbya majuscula JHB graph separating MITE's stereo-unspecified JamD bromination model from its named jamaicamide A biosynthetic-role assignment. Native reference identity is verified; primary catalysis, exact chemical stereochemistry and pathway order are not.

Subject	Predicate	Object	Notes	Evidence
Jamaicamide B (MITE model; stereochemistry unspecified)	is_database_asserted_substrate_of	Lyngbya majuscula JHB JamD	MITE's literal, stereo-unspecified B substrate model only. It is not grounded to the distinct full-key jamaicamide B record.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json https://www.uniprot.org/uniprotkb/Q6E7K6/entry https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet Bromination of jamaicamide B to jamaicamide A. notes MITE0000076 version 2, active, assigns this literal reaction to JamD/Q6E7K6/AAS98776.1/BGC0001001. Its heterologous-expression and in-vitro-assay codes cite DOI:10.1021/jacs.3c05750, which was inaccessible in this pass. These codes are database annotations, not newly verified primary experiments. The example is flagged isIntermediate: true; neither terminal pathway order nor a balanced reaction is inferred. The separate iodination-to-jamaicamide-F example is not adopted here. reference https://www.uniprot.org/uniprotkb/Q6E7K6/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-08 notes UniProtKB Q6E7K6, unreviewed TrEMBL entry 33/sequence 1, annotation 2025-02-05, identifies a 683-aa JamD reference from Lyngbya majuscula, NCBITaxon:158786, with the JHB nucleotide sequence reference and AY522504/AAS98776.1 cross-reference. Protein existence is Predicted, and this response has no catalytic-function comment. It supplies identity, not independent evidence for MITE's functional claim. reference https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet JamD [Lyngbya majuscula] notes GenPept AAS98776.1 names strain JHB, taxon 158786, and coded_by AY522504.1:10463..12514, table 11. Its full 683-aa sequence equals UniProtKB:Q6E7K6. The source calls the protein a putative halogenase possibly involved in alkynyl bromide formation; that native-reference annotation does not verify a historical assay construct or the later enzymatic experiment. reference https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes Independent native-reference audit: AY522504.1 is the 69,900-nt JHB jamaicamide cluster reference named by this owner's BGC0001001. Its complete plus-strand JamD CDS, 10463..12514 (1-based inclusive), contains 2,052 nt, codon_start 1/table 11. Complete-CDS translation equals the 683-aa native CDS annotation, GenPept and UniProt. Native sequence identity does not establish assay-stock identity, catalysis, native production or stereochemistry. reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes RDKit 2026.03.5 literal-SMILES audit, without SMARTS execution: the B model is KZVHAGNFWJIOMX-UHFFFAOYSA-N (C27H37ClN2O4); the A model is NAIKIJSSBJHCBL-UHFFFAOYSA-N (C27H36BrClN2O4). Both are neutral. The corresponding record keys are KZVHAGNFWJIOMX-GDKFLGFMSA-N and NAIKIJSSBJHCBL-IPUGVWFUSA-N. Their connectivity, formula and charge agree, but three specified double-bond configurations in each owner are unspecified in the source model. Both sides also have two unspecified tetrahedral centers. No stereochemistry is completed or inverted and no exact-owner product assignment is made.
Lyngbya majuscula JHB JamD	has_database_asserted_product	Jamaicamide A (MITE model; stereochemistry unspecified)	MITE's literal A model only, not the stereochemically more specified owner. The isIntermediate flag is retained as a source qualification rather than converted into a pathway-order claim.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json https://www.uniprot.org/uniprotkb/Q6E7K6/entry https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet Bromination of jamaicamide B to jamaicamide A. notes MITE0000076 version 2, active, assigns this literal reaction to JamD/Q6E7K6/AAS98776.1/BGC0001001. Its heterologous-expression and in-vitro-assay codes cite DOI:10.1021/jacs.3c05750, which was inaccessible in this pass. These codes are database annotations, not newly verified primary experiments. The example is flagged isIntermediate: true; neither terminal pathway order nor a balanced reaction is inferred. The separate iodination-to-jamaicamide-F example is not adopted here. reference https://www.uniprot.org/uniprotkb/Q6E7K6/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-08 notes UniProtKB Q6E7K6, unreviewed TrEMBL entry 33/sequence 1, annotation 2025-02-05, identifies a 683-aa JamD reference from Lyngbya majuscula, NCBITaxon:158786, with the JHB nucleotide sequence reference and AY522504/AAS98776.1 cross-reference. Protein existence is Predicted, and this response has no catalytic-function comment. It supplies identity, not independent evidence for MITE's functional claim. reference https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet JamD [Lyngbya majuscula] notes GenPept AAS98776.1 names strain JHB, taxon 158786, and coded_by AY522504.1:10463..12514, table 11. Its full 683-aa sequence equals UniProtKB:Q6E7K6. The source calls the protein a putative halogenase possibly involved in alkynyl bromide formation; that native-reference annotation does not verify a historical assay construct or the later enzymatic experiment. reference https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes Independent native-reference audit: AY522504.1 is the 69,900-nt JHB jamaicamide cluster reference named by this owner's BGC0001001. Its complete plus-strand JamD CDS, 10463..12514 (1-based inclusive), contains 2,052 nt, codon_start 1/table 11. Complete-CDS translation equals the 683-aa native CDS annotation, GenPept and UniProt. Native sequence identity does not establish assay-stock identity, catalysis, native production or stereochemistry. reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes RDKit 2026.03.5 literal-SMILES audit, without SMARTS execution: the B model is KZVHAGNFWJIOMX-UHFFFAOYSA-N (C27H37ClN2O4); the A model is NAIKIJSSBJHCBL-UHFFFAOYSA-N (C27H36BrClN2O4). Both are neutral. The corresponding record keys are KZVHAGNFWJIOMX-GDKFLGFMSA-N and NAIKIJSSBJHCBL-IPUGVWFUSA-N. Their connectivity, formula and charge agree, but three specified double-bond configurations in each owner are unspecified in the source model. Both sides also have two unspecified tetrahedral centers. No stereochemistry is completed or inverted and no exact-owner product assignment is made.
Lyngbya majuscula JHB JamD	is_database_assigned_biosynthetic_enzyme_for	Jamaicamide A (owner; three alkene configurations retained)	MITE names jamaicamide A as the product associated with JamD. This records that database-level biosynthetic assignment separately from the model-only reaction, without asserting full chemical equivalence or a newly inspected assay. MITE assigns JamD to jamaicamide B-to-A bromination. Its literal B and A models have the respective owners' connectivity, formula and charge but omit all three alkene configurations retained by those owners. Both models and owners leave two tetrahedral centers unspecified. This is missing stereochemistry, not a demonstrated stereochemical conflict or an exact full-InChIKey join. The models remain separate from the grounded record. Primary assays and constructs were not inspected, so the pathway entry remains proposed; no exact chemical conversion of the owner, balanced reaction, physiological order or native production experiment is asserted.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json https://www.uniprot.org/uniprotkb/Q6E7K6/entry https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet Bromination of jamaicamide B to jamaicamide A. notes MITE0000076 version 2, active, assigns this literal reaction to JamD/Q6E7K6/AAS98776.1/BGC0001001. Its heterologous-expression and in-vitro-assay codes cite DOI:10.1021/jacs.3c05750, which was inaccessible in this pass. These codes are database annotations, not newly verified primary experiments. The example is flagged isIntermediate: true; neither terminal pathway order nor a balanced reaction is inferred. The separate iodination-to-jamaicamide-F example is not adopted here. reference https://www.uniprot.org/uniprotkb/Q6E7K6/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-08 notes UniProtKB Q6E7K6, unreviewed TrEMBL entry 33/sequence 1, annotation 2025-02-05, identifies a 683-aa JamD reference from Lyngbya majuscula, NCBITaxon:158786, with the JHB nucleotide sequence reference and AY522504/AAS98776.1 cross-reference. Protein existence is Predicted, and this response has no catalytic-function comment. It supplies identity, not independent evidence for MITE's functional claim. reference https://www.ncbi.nlm.nih.gov/protein/AAS98776.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-08 snippet JamD [Lyngbya majuscula] notes GenPept AAS98776.1 names strain JHB, taxon 158786, and coded_by AY522504.1:10463..12514, table 11. Its full 683-aa sequence equals UniProtKB:Q6E7K6. The source calls the protein a putative halogenase possibly involved in alkynyl bromide formation; that native-reference annotation does not verify a historical assay construct or the later enzymatic experiment. reference https://www.ncbi.nlm.nih.gov/nuccore/AY522504.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes Independent native-reference audit: AY522504.1 is the 69,900-nt JHB jamaicamide cluster reference named by this owner's BGC0001001. Its complete plus-strand JamD CDS, 10463..12514 (1-based inclusive), contains 2,052 nt, codon_start 1/table 11. Complete-CDS translation equals the 683-aa native CDS annotation, GenPept and UniProt. Native sequence identity does not establish assay-stock identity, catalysis, native production or stereochemistry. reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000076.json evidence type CURATOR_INFERENCE retrieved on 2026-10-08 notes RDKit 2026.03.5 literal-SMILES audit, without SMARTS execution: the B model is KZVHAGNFWJIOMX-UHFFFAOYSA-N (C27H37ClN2O4); the A model is NAIKIJSSBJHCBL-UHFFFAOYSA-N (C27H36BrClN2O4). Both are neutral. The corresponding record keys are KZVHAGNFWJIOMX-GDKFLGFMSA-N and NAIKIJSSBJHCBL-IPUGVWFUSA-N. Their connectivity, formula and charge agree, but three specified double-bond configurations in each owner are unspecified in the source model. Both sides also have two unspecified tetrahedral centers. No stereochemistry is completed or inverted and no exact-owner product assignment is made.

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

Explore across X-Mech

AntibioticMech (jamaicamide A) ↗ MediaIngredientMech (naturalproductmech:mibig-0ce6527209) ↗ TaxonMech: Lyngbya majuscula (NCBITaxon:158786) ↗ PathwayMech (mibig:BGC0001001) ↗

Provenance

Source concept	Source	Version
BGC0001001	MIBIG	5

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