albaflavenone

CHEBI:51460 EXACT SEEDED antimicrobial unspecified

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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A carbotricyclic compound that is (+)-epi-isozizaene in which the hydrogens at position 5 have been replaced by an oxo group.

Structure

Standard InChIKey	SHUZZAXJEJPUGA-CCUNJIBTSA-N
SMILES	C[C@H]1CC(=O)C2=C(C)C(C)(C)[C@H]3CC[C@@]12C3
Stereochemistry	fully defined
Cross-references	npatlas:NPA017239, pubchem:25137938

Filing pathway

Terpenoids — 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 terpene, 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
Streptomyces coelicolor A3(2) NCBITaxon:100226	SOURCE_ASSERTION	mibig:BGC0000660	PMID:18234666

Occurrences 22

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
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1007/S00253-015-7060-9
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1007/S00253-019-10240-3
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1007/S10295-013-1383-2
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1007/S10295-015-1685-7
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1007/S10295-019-02172-8
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1016/B978-0-12-404634-4.00014-0
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1021/JA901313V
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1074/JBC.M710421200
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1111/J.1742-4658.2011.08447.X
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.1128/JB.00017-11
Streptomyces albidoflavus NCBITaxon:1886	LOTUS	DOI:10.7164/ANTIBIOTICS.47.434
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1007/S00253-015-7060-9
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1007/S00253-019-10240-3
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1007/S10295-013-1383-2
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1007/S10295-015-1685-7
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1007/S10295-019-02172-8
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1016/B978-0-12-404634-4.00014-0
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1021/JA901313V
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1074/JBC.M710421200
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1111/J.1742-4658.2011.08447.X
Streptomyces coelicolor NCBITaxon:1902	LOTUS	DOI:10.1128/JB.00017-11
Streptomyces coelicolor A3(2) NCBITaxon:100226	CHEBI	PMID:22151149

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000660	Streptomyces coelicolor A3(2) NCBITaxon:100226	CLUSTER_UNSTATED	genbank:AL645882.2

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	Cyc1 epi-isozizaene synthase UniProtKB:Q9K499	RHEA:25992	CHEBI:175763 → CHEBI:51458	DOI:10.1021/ja061292s
2	CYP170A1 albaflavenone monooxygenase UniProtKB:Q9K498	RHEA:32440	CHEBI:51458 → CHEBI:51460	DOI:10.1074/JBC.M710421200
3	CYP170B1 (S. albus; sequence ungrounded)		CHEBI:51458 → CHEBI:51460	DOI:10.1111/j.1742-4658.2011.08447.x

Entry 1: Cyc1/SCO5222 cyclizes (2E,6E)-farnesyl diphosphate to the (+)-epi-isozizaene committed intermediate in albaflavenone biosynthesis.

Entry 2: CYP170A1/SCO5223 oxidizes (+)-epi-isozizaene through albaflavenol intermediates to albaflavenone.

Entry 3: Reported S. albus ATCC 2396 protein; exact accession, construct sequence and strain alias unresolved. This alternative assay is not a continuation of the S. coelicolor steps. No new stereochemical determination, native-partner assignment or producer upgrade.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 5 nodes, 4 edges

Partial Streptomyces coelicolor albaflavenone biosynthesis graph for Cyc1-catalyzed sesquiterpene cyclization and CYP170A1-catalyzed oxidation to albaflavenone.

Subject	Predicate	Object	Evidence
(2E,6E)-farnesyl diphosphate	is cyclized by	Cyc1	DOI:10.1021/ja061292s reference DOI:10.1021/ja061292s evidence type PRIMARY_EXPERIMENT snippet Molecular cloning and characterization of a new sesquiterpene synthase notes UniProtKB:Q9K499 resolves to the Streptomyces coelicolor A3(2) cyc1/SCO5222 gene product, maps to EMBL AL939123 protein CAB94607.1, and annotates RHEA:25992 for (+)-epi-isozizaene formation.
Cyc1	forms	(+)-epi-isozizaene	DOI:10.1021/ja061292s reference DOI:10.1021/ja061292s evidence type PRIMARY_EXPERIMENT snippet Molecular cloning and characterization of a new sesquiterpene synthase notes UniProtKB:Q9K499 resolves to the Streptomyces coelicolor A3(2) cyc1/SCO5222 gene product, maps to EMBL AL939123 protein CAB94607.1, and annotates RHEA:25992 for (+)-epi-isozizaene formation.
(+)-epi-isozizaene	is oxidized by	CYP170A1	DOI:10.1074/JBC.M710421200 reference DOI:10.1074/JBC.M710421200 evidence type PRIMARY_EXPERIMENT snippet Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2) notes UniProtKB:Q9K498 resolves to the adjacent Streptomyces coelicolor A3(2) SCO5223 gene product, maps to EMBL AL939123 protein CAB94608.1, and annotates the composite left-to-right RHEA:32440 reaction for CYP170A1 oxidation of (+)-epi-isozizaene to albaflavenone.
CYP170A1	forms	albaflavenone	DOI:10.1074/JBC.M710421200 reference DOI:10.1074/JBC.M710421200 evidence type PRIMARY_EXPERIMENT snippet Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2) notes UniProtKB:Q9K498 resolves to the adjacent Streptomyces coelicolor A3(2) SCO5223 gene product, maps to EMBL AL939123 protein CAB94608.1, and annotates the composite left-to-right RHEA:32440 reaction for CYP170A1 oxidation of (+)-epi-isozizaene to albaflavenone.

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

Causal graph — biosynthesis 2 nodes, 1 edge

Source-named CYP170B1 assay; no defensible sequence accession selected. Q82IV2 and Q9K498 denote other organisms, not this protein.

Subject	Predicate	Object	Notes	Evidence
CYP170B1 (S. albus; sequence ungrounded)	catalyzes_formation_from_epi_isozizaene_in_vitro	albaflavenone	Functional assignment is experimental; sequence grounding is unresolved.	DOI:10.1111/j.1742-4658.2011.08447.x reference DOI:10.1111/j.1742-4658.2011.08447.x evidence type PRIMARY_EXPERIMENT snippet CYP170B1 can catalyze the conversion of epi-isozizaene to albaflavenone retrieved on 2026-10-09 notes Results and Methods read. GC/MS comparison with an authentic standard; recombinant C-terminally tagged enzyme with E. coli redox partners. Figure pixels and SI uninspected; later HTTP403.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:51460 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (albaflavenone) ↗ MediaIngredientMech (CHEBI:51460) ↗ TaxonMech: Streptomyces coelicolor A3(2) (NCBITaxon:100226) ↗ PathwayMech (mibig:BGC0000660) ↗

Provenance

Source concept	Source	Version
BGC0000660	MIBIG	5
CHEBI:51460	CHEBI	3-star

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