sesterfisheric acid

naturalproductmech:mibig-90c066a9a2 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	SLCDJJDPKICHGM-ZIFIXUEUSA-N
SMILES	C/C1=C2\CC[C@@H](C)[C@@H]2CC[C@H](C)[C@H]2C[C@@]3(C(=O)O)CC[C@H](C(C)C)[C@@H]3C[C@]12O
Stereochemistry	fully defined
Cross-references	npatlas:NPA032824, pubchem:122209991

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
2	NfP450 cytochrome P450 monooxygenase UniProtKB:A1DN29		CHEBI:138046 → naturalproductmech:mibig-90c066a9a2	DOI:10.1021/jacs.5b08319

Step 1: NfSS cyclizes (2E,6E,10E,14E)-geranylfarnesyl diphosphate to the tetracyclic sesterterpene alcohol sesterfisherol in the first step (RHEA:54068) prior to downstream NfP450 (UniProtKB:A1DN29) oxidation to sesterfisheric acid.

Step 2: Aspergillus fischeri (Neosartorya fischeri) NRRL 181 cytochrome P450 monooxygenase NfP450 (NFIA_055490 / EAW16200.1) oxidizes sesterfisherol (CHEBI:138046) to sesterfisheric acid (naturalproductmech:mibig-90c066a9a2).

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 5 nodes, 4 edges

Aspergillus fischeri NRRL 181 BGC0002162 sesterterpenoid pathway: bifunctional sesterfisherol synthase NfSS (NFIA_055500) converts (2E,6E,10E,14E)-geranylfarnesyl diphosphate to sesterfisherol, and adjacent cytochrome P450 monooxygenase NfP450 (NFIA_055490) oxidizes sesterfisherol to sesterfisheric acid.

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.
sesterfisherol	is oxidized by	NfP450 cytochrome P450 monooxygenase	NfP450 oxidizes sesterfisherol in the second step of sesterfisheric acid biosynthesis.	DOI:10.1021/jacs.5b08319 https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk https://www.uniprot.org/uniprotkb/A1DN29 reference DOI:10.1021/jacs.5b08319 evidence type PRIMARY_EXPERIMENT snippet Finally, the cryptic sesterterpene synthase (NfSS) and an adjacent cytochrome P450 (NfP450) from Neosartorya fischeri were identified and shown to guide the synthesis of sesterfisherol (1) and sesterfisheric acid (2), respectively. notes Ye et al. (2015) co-expressed Neosartorya fischeri (Aspergillus fischeri NRRL 181) NfSS (NFIA_055500) and the adjacent cytochrome P450 monooxygenase NfP450 (NFIA_055490) in Aspergillus oryzae NSAR1 and demonstrated that NfP450 oxidizes sesterfisherol (1) to sesterfisheric acid (2). reference https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-23 notes MIBiG BGC0002162.3 spans Aspergillus fischeri NRRL 181 DS027698.1 2485363..2490827, encoding NFIA_055500 (EAW16201.1, UniProtKB:A1DN30, NfSS) and NFIA_055490 (EAW16200.1, UniProtKB:A1DN29, NfP450) for sesterfisherol and sesterfisheric acid biosynthesis. reference https://www.uniprot.org/uniprotkb/A1DN29 evidence type DATABASE_ASSERTION retrieved on 2026-10-23 notes UniProtKB:A1DN29 is the Aspergillus fischeri NRRL 181 NFIA_055490 (EAW16200.1) cytochrome P450 monooxygenase encoded adjacent to NfSS (NFIA_055500, EAW16201.1, UniProtKB:A1DN30) in BGC0002162.
NfP450 cytochrome P450 monooxygenase	forms	sesterfisheric acid	Heterologous co-expression of NfSS and NfP450 in Aspergillus oryzae NSAR1 yields sesterfisheric acid.	DOI:10.1021/jacs.5b08319 https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk https://www.uniprot.org/uniprotkb/A1DN29 reference DOI:10.1021/jacs.5b08319 evidence type PRIMARY_EXPERIMENT snippet Finally, the cryptic sesterterpene synthase (NfSS) and an adjacent cytochrome P450 (NfP450) from Neosartorya fischeri were identified and shown to guide the synthesis of sesterfisherol (1) and sesterfisheric acid (2), respectively. notes Ye et al. (2015) co-expressed Neosartorya fischeri (Aspergillus fischeri NRRL 181) NfSS (NFIA_055500) and the adjacent cytochrome P450 monooxygenase NfP450 (NFIA_055490) in Aspergillus oryzae NSAR1 and demonstrated that NfP450 oxidizes sesterfisherol (1) to sesterfisheric acid (2). reference https://mibig.secondarymetabolites.org/repository/BGC0002162.3/BGC0002162.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-23 notes MIBiG BGC0002162.3 spans Aspergillus fischeri NRRL 181 DS027698.1 2485363..2490827, encoding NFIA_055500 (EAW16201.1, UniProtKB:A1DN30, NfSS) and NFIA_055490 (EAW16200.1, UniProtKB:A1DN29, NfP450) for sesterfisherol and sesterfisheric acid biosynthesis. reference https://www.uniprot.org/uniprotkb/A1DN29 evidence type DATABASE_ASSERTION retrieved on 2026-10-23 notes UniProtKB:A1DN29 is the Aspergillus fischeri NRRL 181 NFIA_055490 (EAW16200.1) cytochrome P450 monooxygenase encoded adjacent to NfSS (NFIA_055500, EAW16201.1, UniProtKB:A1DN30) in BGC0002162.

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

Explore across X-Mech

AntibioticMech (sesterfisheric acid) ↗ MediaIngredientMech (naturalproductmech:mibig-90c066a9a2) ↗ TaxonMech: Aspergillus fischeri NRRL 181 (NCBITaxon:331117) ↗ PathwayMech (mibig:BGC0002162) ↗

Provenance

Source concept	Source	Version
BGC0002162	MIBIG	3

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