capsidiol

CHEBI:28283 EXACT SEEDED antifungal

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

An eremophilane sesquiterpenoid that is (+)-5-epi-aristolochene bearing additional 1β- and 3α-hydroxy substituents. It is a phytoalexin produced in Nicotiana and Capsicum plant species in response to pathogen attack.

Structure

Standard InChIKey	BXXSHQYDJWZXPB-OKNSCYNVSA-N
SMILES	C[C@@H]1[C@@H](C[C@H](C2=CC[C@H](C[C@]12C)C(=C)C)O)O
Stereochemistry	fully defined
Cross-references	pubchem:161937

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
Nicotiana tabacum NCBITaxon:4097	SOURCE_ASSERTION	mibig:BGC0001997	DOI:10.1007/s00425-019-03255-7

Occurrences 24

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
Nicotiana fragrans NCBITaxon:118697	LOTUS	DOI:10.1016/S0031-9422(00)83008-3
Nicotiana forsteri NCBITaxon:1209491	LOTUS	DOI:10.1016/S0031-9422(00)83008-3
Capsicum annuum var. annuum NCBITaxon:40321	LOTUS	DOI:10.1021/JF061404Z
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1007/BF00232372
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1016/S0031-9422(00)81559-9
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1016/S0031-9422(00)89733-2
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1021/JF00012A010
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1021/NP0305472
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.1271/BBB.58.305
Capsicum annuum NCBITaxon:4072	LOTUS	DOI:10.55730/1300-011X.2893
Capsicum annuum NCBITaxon:4072	CHEBI	PMID:24178358
Nicotiana debneyi NCBITaxon:4089	LOTUS	DOI:10.1016/S0031-9422(00)83008-3
Nicotiana benthamiana NCBITaxon:4100	CHEBI	PMID:34395763
Nicotiana clevelandii NCBITaxon:81866	LOTUS	DOI:10.1016/0031-9422(75)85148-X
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1007/S00425-019-03255-7
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(75)85148-X
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(79)80035-7
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(80)85086-2
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(88)80195-X
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(88)87028-6
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(91)83608-N
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/0031-9422(94)85059-3
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/S0031-9422(00)83009-5
Nicotiana tabacum NCBITaxon:4097	LOTUS	DOI:10.1016/S0031-9422(00)84695-6

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001997	Nicotiana tabacum NCBITaxon:4097	CLUSTER_UNSTATED	genbank:NCAA01001461.1

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
1	CYP71D20 5-epiaristolochene 1,3-dihydroxylase UniProtKB:Q94FM7	RHEA:28226	CHEBI:23925 + CHEBI:57618 + CHEBI:15379 → CHEBI:28283 + CHEBI:58210 + CHEBI:15377 + CHEBI:15378	DOI:10.1006/abbi.2001.2483

Step 1: CYP71D20 carries out the terminal two hydroxylations from (+)-5-epi-aristolochene to capsidiol in Nicotiana tabacum; RHEA:28226 grounds the full reduced-NADPH--hemoprotein-reductase-dependent monooxygenase reaction. The seeded BGC0001997 locus has anonymous antiSMASH P450 predictions and is not used here as exact CYP71D20 locus evidence.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Nicotiana tabacum capsidiol biosynthesis graph for CYP71D20-catalyzed 5-epi-aristolochene hydroxylation.

Subject	Predicate	Object	Notes	Evidence
(+)-5-epi-aristolochene	is hydroxylated by	CYP71D20 5-epiaristolochene 1,3-dihydroxylase	CYP71D20 hydroxylates 5-epi-aristolochene, with 1beta-hydroxy-5-epi-aristolochene favored as the released monohydroxylated intermediate before the second hydroxylation that yields capsidiol.	DOI:10.1006/abbi.2001.2483 DOI:10.1074/jbc.M411870200 https://www.uniprot.org/uniprotkb/Q94FM7 https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv reference DOI:10.1006/abbi.2001.2483 evidence type PRIMARY_EXPERIMENT snippet CYP71D20-encoded enzyme activity was capable of converting both 5-epi-aristolochene and 1-deoxycapsidiol to capsidiol in vitro notes Ralston et al. cloned full-length Nicotiana tabacum CYP71D20 cDNA, registered GenBank AF368376, expressed representative P450s in yeast, and assayed microsomal 5-epiaristolochene hydroxylase activity. reference DOI:10.1074/jbc.M411870200 evidence type PRIMARY_EXPERIMENT snippet The final step of capsidiol biosynthesis is catalyzed by 5-epiaristolochene dihydroxylase notes Takahashi et al. measured purified CYP71D20/EAH kinetics with 5-epi-aristolochene and monohydroxylated deoxycapsidiol intermediates, supporting successive C1 and C3 hydroxylations. reference https://www.uniprot.org/uniprotkb/Q94FM7 evidence type DATABASE_ASSERTION snippet Involved in the biosynthesis of capsidiol retrieved on 2026-09-30 notes Reviewed UniProtKB:Q94FM7 is the 504 aa Nicotiana tabacum 5-epiaristolochene 1,3-dihydroxylase, carries CYP71D20 as the gene name, cross-references GenBank AF368376 protein AAK62342.2, and annotates RHEA:28226 from PMIDs 12504906, 15522862, and 17715131. reference https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes The Rhea Swiss-Prot mapping links RHEA:28226 to UniProtKB:Q94FM7.
CYP71D20 5-epiaristolochene 1,3-dihydroxylase	forms	capsidiol	The CYP71D20 cytochrome P450 reaction forms capsidiol by successive C1 and C3 hydroxylations of 5-epi-aristolochene.	DOI:10.1006/abbi.2001.2483 DOI:10.1074/jbc.M411870200 https://www.uniprot.org/uniprotkb/Q94FM7 https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv reference DOI:10.1006/abbi.2001.2483 evidence type PRIMARY_EXPERIMENT snippet CYP71D20-encoded enzyme activity was capable of converting both 5-epi-aristolochene and 1-deoxycapsidiol to capsidiol in vitro notes Ralston et al. cloned full-length Nicotiana tabacum CYP71D20 cDNA, registered GenBank AF368376, expressed representative P450s in yeast, and assayed microsomal 5-epiaristolochene hydroxylase activity. reference DOI:10.1074/jbc.M411870200 evidence type PRIMARY_EXPERIMENT snippet The final step of capsidiol biosynthesis is catalyzed by 5-epiaristolochene dihydroxylase notes Takahashi et al. measured purified CYP71D20/EAH kinetics with 5-epi-aristolochene and monohydroxylated deoxycapsidiol intermediates, supporting successive C1 and C3 hydroxylations. reference https://www.uniprot.org/uniprotkb/Q94FM7 evidence type DATABASE_ASSERTION snippet Involved in the biosynthesis of capsidiol retrieved on 2026-09-30 notes Reviewed UniProtKB:Q94FM7 is the 504 aa Nicotiana tabacum 5-epiaristolochene 1,3-dihydroxylase, carries CYP71D20 as the gene name, cross-references GenBank AF368376 protein AAK62342.2, and annotates RHEA:28226 from PMIDs 12504906, 15522862, and 17715131. reference https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes The Rhea Swiss-Prot mapping links RHEA:28226 to UniProtKB:Q94FM7.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:28283 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (capsidiol) ↗ MediaIngredientMech (CHEBI:28283) ↗ TaxonMech: Nicotiana tabacum (NCBITaxon:4097) ↗ PathwayMech (mibig:BGC0001997) ↗

Provenance

Source concept	Source	Version
BGC0001997	MIBIG	3
CHEBI:28283	CHEBI	3-star

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