sanglifehrin A

naturalproductmech:mibig-472be7e9b4 MINTED SEEDED enzyme inhibitor

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	ONJZYZYZIKTIEG-CFBQITSMSA-N
SMILES	CC[C@H]1C[C@H](C)[C@@]2(NC1=O)O[C@@H](C[C@H](O)[C@@H](C)CC\C=C\C=C(/C)[C@@H]1C\C=C\C=C\[C@H](O)[C@H](C)[C@@H](O)[C@@H](CCC(C)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC3=CC(O)=CC=C3)C(=O)N3CCC[C@H](N3)C(=O)O1)[C@H](C)[C@H](O)[C@@H]2C
Stereochemistry	fully defined
Cross-references	npatlas:NPA014131, pubchem:5388925

Filing pathway

Amino acids and peptides — 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, pks, 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 flaveolus NCBITaxon:67297	SOURCE_ASSERTION	mibig:BGC0001042	PMID:21416665

Occurrences 2

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 NCBITaxon:1883	LOTUS	DOI:10.7164/ANTIBIOTICS.52.466
Streptomyces NCBITaxon:1883	LOTUS	DOI:10.7164/ANTIBIOTICS.52.474

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001042	Streptomyces flaveolus NCBITaxon:67297	CLUSTER_UNSTATED	genbank:FJ809786.1

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.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 2 nodes, 1 edge

Sanglifehrin A binds human cyclophilin A in the PDB 1YND co-crystal structure.

Subject	Predicate	Object	Notes	Evidence
sanglifehrin A	binds	human cyclophilin A	PubChem BioAssay AID 977608 maps this exact Standard InChIKey to an active 0.0036 uM IC50 row for PDB 1YND chain A; PDBe maps 1YND_A to Homo sapiens UniProtKB:P62937, and RCSB reports SFA sanglifehrin A with the record's Standard InChIKey as a 1YND non-polymer ligand.	DOI:10.1074/jbc.M501623200 DOI:10.2210/pdb1ynd/pdb reference DOI:10.1074/jbc.M501623200 evidence type PRIMARY_EXPERIMENT snippet Structure of human cyclophilin A in complex with the novel immunosuppressant sanglifehrin A at 1.6 A resolution. notes Kallen et al. solved PDB 1YND as a sanglifehrin-A-bound human cyclophilin A structure. reference DOI:10.2210/pdb1ynd/pdb evidence type DATABASE_ASSERTION notes RCSB PDB identifies 1YND as a human cyclophilin A crystal structure containing SFA sanglifehrin A, and PDBe maps chain A to the complete canonical Homo sapiens PPIA sequence in UniProtKB:P62937.

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

Bioactivities 2

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB	IC50 0.0036 uM; ACTIVE	Not recorded	PMID:15772070 assay Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB evidence reference PMID:15772070 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 977608, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1YND_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 0.0036 units uM activity class ENZYME_INHIBITOR
Experimentally measured binding affinity data derived from PDB	ACTIVE	Not recorded	PMID:15772070 assay Experimentally measured binding affinity data derived from PDB evidence reference PMID:15772070 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1811, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1YND_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE activity class ENZYME_INHIBITOR

Explore across X-Mech

AntibioticMech (sanglifehrin A) ↗ MediaIngredientMech (naturalproductmech:mibig-472be7e9b4) ↗ TaxonMech: Streptomyces flaveolus (NCBITaxon:67297) ↗ PathwayMech (mibig:BGC0001042) ↗

Provenance

Source concept	Source	Version
BGC0001042	MIBIG	5

This page is generated from data/natural_products/amino_acids_and_peptides/sanglifehrin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.