sesterfisherol

CHEBI:138046 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 tetracyclic sesterterpenoid obtained by by expressing a small gene cluster consisting of a terpene synthase (Nf SS) and a cytochrome P450 monooxygenase (Nf P450).

Structure

Standard InChIKey	VQMHZILKNHUAMP-AISFCYSSSA-N
SMILES	C/C1=C2\CC[C@@H](C)[C@@H]2CC[C@H](C)[C@H]2C[C@@]3(C)CC[C@H](C(C)C)[C@@H]3C[C@]12O
Stereochemistry	fully defined
Cross-references	npatlas:NPA032823

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
Aspergillus fischeri NRRL 181 NCBITaxon:331117	SOURCE_ASSERTION	mibig:BGC0002162	DOI:10.1021/jacs.5b08319

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
Aspergillus flavus NCBITaxon:5059	LOTUS	DOI:10.1021/JACS.5B08319

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002162	Aspergillus fischeri NRRL 181 NCBITaxon:331117	CLUSTER_DEMONSTRATED	genbank:DS027698.1

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	NfSS sesterfisherol synthase UniProtKB:A1DN30	RHEA:54068	CHEBI:57907 → CHEBI:138046	DOI:10.1021/jacs.5b08319

Step 1: NfSS cyclizes (2E,6E,10E,14E)-geranylfarnesyl diphosphate to the tetracyclic sesterterpene alcohol sesterfisherol. This single step records the sesterfisherol-forming RHEA:54068 reaction and leaves the downstream A1DN29/NfP450 oxidation to sesterfisheric acid unexpanded.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Aspergillus fischeri NRRL 181 NfSS cyclizes (2E,6E,10E,14E)-geranylfarnesyl diphosphate to form sesterfisherol.

Subject	Predicate	Object	Notes	Evidence
(2E,6E,10E,14E)-geranylfarnesyl diphosphate	is cyclized by	NfSS	NfSS is the bifunctional terpene synthase whose cyclase domain converts geranylfarnesyl diphosphate to the 5-6-8-5 tetracyclic sesterfisherol scaffold.	DOI:10.1021/jacs.5b08319 https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk https://www.uniprot.org/uniprotkb/A1DN30 https://www.rhea-db.org/rhea/54068 reference DOI:10.1021/jacs.5b08319 evidence type PRIMARY_EXPERIMENT snippet identified the sesterfisherol synthase gene (NfSS) from Neosartorya fischeri notes Ye et al. used Aspergillus oryzae heterologous expression to functionally characterize NfSS and assigned its terpene cyclase product as the 5-6-8-5 tetracyclic C25 alcohol sesterfisherol. reference https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002162.3 maps the Aspergillus fischeri NRRL 181 / Neosartorya fischeri DS027698 sesterfisherol cluster CDS NFIA_055500 to GenPept EAW16201.1. reference https://www.uniprot.org/uniprotkb/A1DN30 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:A1DN30 is the 764 aa Aspergillus fischeri NRRL 181 NfSS/NFIA_055500 sesterfisherol synthase, cross-references EMBL DS027698 protein EAW16201.1, and cites DOI:10.1021/jacs.5b08319. reference https://www.rhea-db.org/rhea/54068 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:54068 is the (2E,6E,10E,14E)-geranylfarnesyl diphosphate plus water to sesterfisherol plus diphosphate reaction; Rhea maps the master reaction to UniProtKB:A1DN30 in Swiss-Prot.
NfSS	forms	sesterfisherol	Heterologous NfSS expression assigned the Aspergillus fischeri / Neosartorya fischeri enzyme as the sesterfisherol synthase.	DOI:10.1021/jacs.5b08319 https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk https://www.uniprot.org/uniprotkb/A1DN30 https://www.rhea-db.org/rhea/54068 reference DOI:10.1021/jacs.5b08319 evidence type PRIMARY_EXPERIMENT snippet identified the sesterfisherol synthase gene (NfSS) from Neosartorya fischeri notes Ye et al. used Aspergillus oryzae heterologous expression to functionally characterize NfSS and assigned its terpene cyclase product as the 5-6-8-5 tetracyclic C25 alcohol sesterfisherol. reference https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002162.3 maps the Aspergillus fischeri NRRL 181 / Neosartorya fischeri DS027698 sesterfisherol cluster CDS NFIA_055500 to GenPept EAW16201.1. reference https://www.uniprot.org/uniprotkb/A1DN30 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:A1DN30 is the 764 aa Aspergillus fischeri NRRL 181 NfSS/NFIA_055500 sesterfisherol synthase, cross-references EMBL DS027698 protein EAW16201.1, and cites DOI:10.1021/jacs.5b08319. reference https://www.rhea-db.org/rhea/54068 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:54068 is the (2E,6E,10E,14E)-geranylfarnesyl diphosphate plus water to sesterfisherol plus diphosphate reaction; Rhea maps the master reaction to UniProtKB:A1DN30 in Swiss-Prot.

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

Explore across X-Mech

AntibioticMech (sesterfisherol) ↗ MediaIngredientMech (CHEBI:138046) ↗ TaxonMech: Aspergillus fischeri NRRL 181 (NCBITaxon:331117) ↗ PathwayMech (mibig:BGC0002162) ↗

Provenance

Source concept	Source	Version
BGC0002162	MIBIG	3
CHEBI:138046	CHEBI	3-star

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