cyclosporin A

CHEBI:4031 EXACT SEEDED antifungalcytotoxic

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 6 nodes, 6 edges

Cyclosporin A binds human cyclophilin A, and the cyclosporin A-cyclophilin A complex binds the human calcineurin A/B phosphatase.

Subject	Predicate	Object	Notes	Evidence
cyclosporin A	binds	human cyclophilin A	PDB 1MF8 contains cyclosporin A as chain D and maps the human cyclophilin A chain C to UniProtKB:P62937.	DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.
cyclosporin A	forms	human cyclophilin A-cyclosporin A complex		DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.
human cyclophilin A	forms	human cyclophilin A-cyclosporin A complex		DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.
human calcineurin A alpha	forms	human calcineurin A/B complex		DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.
human calcineurin B type 1	forms	human calcineurin A/B complex		DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.
human cyclophilin A-cyclosporin A complex	binds	human calcineurin A/B complex	PDB 1MF8 maps human calcineurin A chain A to UniProtKB:Q08209 and human calcineurin B chain B to UniProtKB:P63098.	DOI:10.1073/PNAS.212504399 reference DOI:10.1073/PNAS.212504399 evidence type PRIMARY_EXPERIMENT snippet Crystal Structure of Human Calcineurin Complexed with Cyclosporin a and Human Cyclophilin notes Jin and Harrison solved PDB 1MF8 with human calcineurin A, human calcineurin B, human cyclophilin A, and cyclosporin A.

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

Bioactivities 25

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

Elsewhere in the fleet

AntibioticMech — CHEBI:4031 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (cyclosporin A) ↗ MediaIngredientMech (CHEBI:4031) ↗ TaxonMech: Tolypocladium inflatum NRRL 8044 (NCBITaxon:29910) ↗ PathwayMech (mibig:BGC0000334) ↗

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.

Assay	Result	Target enzyme	Source detail
A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis	OTHER 22.12 uM; ACTIVE	Not recorded	pubchem.aid:435019 assay A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis evidence reference pubchem.aid:435019 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 435019, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. Source endpoint: CC50. call ACTIVE measurement type OTHER value 22.12 units uM activity class CYTOTOXIC
A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol	IC50 99.57 uM; ACTIVE	Not recorded	pubchem.aid:449764 assay A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol evidence reference pubchem.aid:449764 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 449764, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 99.57 units uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology	OTHER 1.5849 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1645839 assay A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology evidence reference pubchem.aid:1645839 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 1.5849 units uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology	OTHER 1.5849 uM; NOT_DETERMINED	UniProtKB:O14656	pubchem.aid:1645839 assay A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology evidence reference pubchem.aid:1645839 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 1.5849 units uM target enzyme UniProtKB:O14656
A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells.	OTHER 0.631 uM; NOT_DETERMINED	Not recorded	pubchem.aid:624297 assay A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. evidence reference pubchem.aid:624297 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624297, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_056979 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 0.631 units uM
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary	OTHER 0.565385 uM; NOT_DETERMINED	Not recorded	pubchem.aid:2061107 assay Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary evidence reference pubchem.aid:2061107 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2061107, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 0.565385 units uM
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary	OTHER 0.565385 uM; NOT_DETERMINED	Not recorded	pubchem.aid:2061107 assay Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay: Summary evidence reference pubchem.aid:2061107 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2061107, deposited by 824; assay type Summary. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_000015 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 0.565385 units uM
Calcineurin Phosphatase (CaN) Assay from US Patent US10077289: "Cyclosporins modified on the MeBmt sidechain by heterocyclic rings"	IC50 0.21 uM; ACTIVE	UniProtKB:P48454	pubchem.aid:1795693 assay Calcineurin Phosphatase (CaN) Assay from US Patent US10077289: "Cyclosporins modified on the MeBmt sidechain by heterocyclic rings" evidence reference pubchem.aid:1795693 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1795693, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.21 units uM target enzyme UniProtKB:P48454
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen	OTHER 10.0541 uM; ACTIVE	Not recorded	pubchem.aid:1346979 assay Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen evidence reference pubchem.aid:1346979 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346979, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 10.0541 units uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen	OTHER 6.6824 uM; ACTIVE	Not recorded	pubchem.aid:1346979 assay Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen evidence reference pubchem.aid:1346979 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346979, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 6.6824 units uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen	OTHER 15.9347 uM; ACTIVE	Not recorded	pubchem.aid:1346981 assay Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen evidence reference pubchem.aid:1346981 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 15.9347 units uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen	OTHER 13.3332 uM; ACTIVE	Not recorded	pubchem.aid:1346981 assay Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen evidence reference pubchem.aid:1346981 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 13.3332 units uM
Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome	OTHER 0.1 uM; NOT_DETERMINED	Not recorded	PMID:33910017 assay Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome evidence reference PMID:33910017 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1508629, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 0.1 units uM
Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R	OTHER 23.1093 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963990 assay Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R evidence reference pubchem.aid:1963990 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963990, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 23.1093 units uM
Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13	OTHER 29.0929 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963989 assay Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 evidence reference pubchem.aid:1963989 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963989, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 29.0929 units uM
Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	OTHER 1.7783 uM; NOT_DETERMINED	Not recorded	PMID:33910017 assay Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay evidence reference PMID:33910017 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1508628, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 1.7783 units uM
Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay	OTHER 8.9125 uM; NOT_DETERMINED	Not recorded	PMID:33910017 assay Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay evidence reference PMID:33910017 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1508627, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 8.9125 units uM
Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof"	KI 0.0091 uM; ACTIVE	UniProtKB:P23284	pubchem.aid:2282760 assay Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof" evidence reference pubchem.aid:2282760 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2282760, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 0.0091 units uM target enzyme UniProtKB:P23284
Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof"	KI 0.0078 uM; ACTIVE	UniProtKB:P62937	pubchem.aid:2282760 assay Cyclophilin Peptidyl-Prolyl Isomerase Functional Assay from US Patent US12522634: "Cyclophilin inhibitors and uses thereof" evidence reference pubchem.aid:2282760 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2282760, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 0.0078 units uM target enzyme UniProtKB:P62937
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay	OTHER 13.1044 uM; ACTIVE	Not recorded	pubchem.aid:1671199 assay Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671199 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 13.1044 units uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay	OTHER 13.1044 uM; ACTIVE	Not recorded	pubchem.aid:1671199 assay Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671199 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession EAW99313 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 13.1044 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 5.8535 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 5.8535 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 5.8535 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAV41877 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 5.8535 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 8.709 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 8.709 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 8.709 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAV41877 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 8.709 units uM notes 318 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.