shinorine

CHEBI:131712 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 mycosporine-like amino acid that is the ketimine resulting from the formal condensation of the amino group of L-serine with the keto group of (5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-one and in which the hydrogen at position 3 of the cyclohexenone moiety has been replaced by the amino group of glycine. It is an active ingredient found in environmentally friendly sunscreen creams.

Structure

Standard InChIKey	WXEQFJUHQIGKNG-MZNRBSSJSA-N
SMILES	O[C@](CC(NCC(O)=O)=C/1OC)(CO)CC1=N/[C@@H](CO)C(O)=O
Stereochemistry	fully defined

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, 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
Trichormus variabilis ATCC 29413 NCBITaxon:240292	SOURCE_ASSERTION	mibig:BGC0000427	PMID:20813918

Occurrences 6

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
Curdiea racovitzia NCBITaxon:2025844	CHEBI	ISBN: 9789401773218
Anabaena variabilis NCBITaxon:264691	LOTUS	DOI:10.1111/J.1751-1097.2008.00376.X
Chondrus crispus NCBITaxon:2769	CHEBI	ISBN: 9789401773218
Palmaria palmata NCBITaxon:2822	CHEBI	ISBN: 9789401773218
Pyropia columbina NCBITaxon:688709	CHEBI	ISBN: 9789401773218
Patiria pectinifera NCBITaxon:7594	LOTUS	DOI:10.1246/CL.1981.1413

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000427	Trichormus variabilis ATCC 29413 NCBITaxon:240292	CLUSTER_DEMONSTRATED	genbank:CP000117.1

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.

Step	Enzyme	Reaction	Substrate → product	Evidence
4	Ava_3855 NRPS-like shinorine synthase UniProtKB:Q3M6C6		naturalproductmech:mibig-00a364fe41 + CHEBI:17115 → CHEBI:131712	DOI:10.1126/science.1193637

Step 4: Trichormus variabilis ATCC 29413 Ava_3855 catalyzes the ATP-dependent terminal serine incorporation step that converts mycosporine glycine to shinorine. No exact Rhea reaction was available for this serine addition.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Trichormus variabilis ATCC 29413 Ava_3855-catalyzed terminal attachment of serine to mycosporine glycine in shinorine biosynthesis.

Subject	Predicate	Object	Notes	Evidence
mycosporine glycine	is converted to shinorine by	Ava_3855	Purified Ava_3855 uses mycosporine glycine and serine as substrates in ATP-dependent shinorine formation.	DOI:10.1126/science.1193637 https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ https://www.uniprot.org/uniprotkb/Q3M6C6 reference DOI:10.1126/science.1193637 evidence type PRIMARY_EXPERIMENT snippet HPLC assays confirmed its role in converting mycosporine glycine and serine to shinorine notes Balskus and Walsh showed that the complete 6.5 kb Ava_3858-Ava_3855 cluster produced shinorine in Escherichia coli, that a construct truncated before Ava_3855 accumulated mycosporine glycine, and that purified Ava_3855 converted mycosporine glycine plus serine to shinorine in an ATP-dependent HPLC assay. reference https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 5 links BGC0000427 to shinorine biosynthesis in Trichormus variabilis ATCC 29413 and lists Ava_3855 / ABA23460.1 at CP000117.1:4798900-4801566 on the minus strand. reference https://www.uniprot.org/uniprotkb/Q3M6C6 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q3M6C6 is the Trichormus variabilis ATCC 29413 / PCC 7937 Ava_3855 amino acid adenylation entry cross-referenced to EMBL CP000117 and GenPept ABA23460.1.
L-serine	is attached to mycosporine glycine by	Ava_3855	Ava_3855 activates serine through its adenylation domain and loads it onto the enzyme thiolation domain before shinorine formation.	DOI:10.1126/science.1193637 https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ https://www.uniprot.org/uniprotkb/Q3M6C6 reference DOI:10.1126/science.1193637 evidence type PRIMARY_EXPERIMENT snippet HPLC assays confirmed its role in converting mycosporine glycine and serine to shinorine notes Balskus and Walsh showed that the complete 6.5 kb Ava_3858-Ava_3855 cluster produced shinorine in Escherichia coli, that a construct truncated before Ava_3855 accumulated mycosporine glycine, and that purified Ava_3855 converted mycosporine glycine plus serine to shinorine in an ATP-dependent HPLC assay. reference https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 5 links BGC0000427 to shinorine biosynthesis in Trichormus variabilis ATCC 29413 and lists Ava_3855 / ABA23460.1 at CP000117.1:4798900-4801566 on the minus strand. reference https://www.uniprot.org/uniprotkb/Q3M6C6 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q3M6C6 is the Trichormus variabilis ATCC 29413 / PCC 7937 Ava_3855 amino acid adenylation entry cross-referenced to EMBL CP000117 and GenPept ABA23460.1.
Ava_3855	forms	shinorine	Full-cluster heterologous expression produced shinorine, while the Ava_3855-truncated construct accumulated mycosporine glycine.	DOI:10.1126/science.1193637 https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ https://www.uniprot.org/uniprotkb/Q3M6C6 reference DOI:10.1126/science.1193637 evidence type PRIMARY_EXPERIMENT snippet HPLC assays confirmed its role in converting mycosporine glycine and serine to shinorine notes Balskus and Walsh showed that the complete 6.5 kb Ava_3858-Ava_3855 cluster produced shinorine in Escherichia coli, that a construct truncated before Ava_3855 accumulated mycosporine glycine, and that purified Ava_3855 converted mycosporine glycine plus serine to shinorine in an ATP-dependent HPLC assay. reference https://mibig.secondarymetabolites.org/repository/BGC0000427.5/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 5 links BGC0000427 to shinorine biosynthesis in Trichormus variabilis ATCC 29413 and lists Ava_3855 / ABA23460.1 at CP000117.1:4798900-4801566 on the minus strand. reference https://www.uniprot.org/uniprotkb/Q3M6C6 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q3M6C6 is the Trichormus variabilis ATCC 29413 / PCC 7937 Ava_3855 amino acid adenylation entry cross-referenced to EMBL CP000117 and GenPept ABA23460.1.

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

Explore across X-Mech

AntibioticMech (shinorine) ↗ MediaIngredientMech (CHEBI:131712) ↗ TaxonMech: Trichormus variabilis ATCC 29413 (NCBITaxon:240292) ↗ PathwayMech (mibig:BGC0000427) ↗

Provenance

Source concept	Source	Version
BGC0000427	MIBIG	5
CHEBI:131712	CHEBI	3-star

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