cyclosporin A
CHEBI:4031 EXACT SEEDED antifungalcytotoxic
A cyclic nonribosomal peptide of eleven amino acids; an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the patient's immune system, and therefore the risk of organ rejection. Also causes reversible inhibition of immunocompetent lymphocytes in the G0- and G1-phase of the cell cycle.
Structure
| Standard InChIKey | PMATZTZNYRCHOR-CGLBZJNRSA-N |
|---|---|
| SMILES | CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:5284373 |
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, 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 |
|---|---|---|---|
| Tolypocladium inflatum NRRL 8044 NCBITaxon:29910 |
SOURCE_ASSERTION | mibig:BGC0000334 | DOI:10.1371/journal.pgen.1003496 |
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 |
|---|---|---|
| Trichoderma polysporum NCBITaxon:40695 |
LOTUS | DOI:10.1002/HLCA.19760590412 |
| Tolypocladium inflatum NCBITaxon:29910 |
LOTUS | DOI:10.1371/JOURNAL.PGEN.1003496 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000334 | Tolypocladium inflatum NRRL 8044 NCBITaxon:29910 |
CLUSTER_UNSTATED | genbank:QEPI01000018.1 |
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.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis | 22.12 uM | pubchem.aid:435019 |
| A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol | IC50 99.57 uM | pubchem.aid:449764 |
| A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology | 1.5849 uM | pubchem.aid:1645839 |
| A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology | 1.5849 uM | pubchem.aid:1645839 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 0.631 uM | pubchem.aid:624297 |
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 0.565385 uM | pubchem.aid:2061107 |
| Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary | 0.565385 uM | pubchem.aid:2061107 |
| Calcineurin Phosphatase (CaN) Assay from US Patent US10077289: "Cyclosporins modified on the MeBmt sidechain by heterocyclic rings" | IC50 0.21 uM | pubchem.aid:1795693 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 10.0541 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 6.6824 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 15.9347 uM | pubchem.aid:1346981 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 13.3332 uM | pubchem.aid:1346981 |
| Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome | 0.1 uM | PMID:33910017 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 23.1093 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 29.0929 uM | pubchem.aid:1963989 |
| Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 1.7783 uM | PMID:33910017 |
| Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay | 8.9125 uM | PMID:33910017 |
| Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof" | KI 0.0091 uM | pubchem.aid:2282760 |
| Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof" | KI 0.0078 uM | pubchem.aid:2282760 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 13.1044 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 13.1044 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 5.8535 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 5.8535 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 8.709 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 8.709 uM | pubchem.aid:1671197 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:4031 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000334 | MIBIG | 4 |
| CHEBI:4031 | CHEBI | 3-star |
This page is generated from data/natural_products/amino_acids_and_peptides/cyclosporin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.