NaturalProductMech

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cycloheximide

naturalproductmech:mibig-ab5ddd856a MINTED SEEDED cytotoxicenzyme 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKeyYPHMISFOHDHNIV-GAIPPQHRSA-N
SMILES[H][C@@](O)(CC1CC(=O)NC(=O)C1)[C@@]1([H])C[C@@H](C)C[C@H](C)C1=O
Stereochemistryfully defined
Cross-referencesnpatlas:NPA012393, pubchem:6197

Filing pathway

Alkaloids — 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 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.

TaxonBasisClusterEvidence
Streptomyces sp. YIM 56141
NCBITaxon:1211968		 BGC_CHARACTERIZED mibig:BGC0000175 PMID:24815182

Occurrences 3

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.

TaxonSourceReference
Streptomyces
NCBITaxon:1883		 LOTUS DOI:10.1021/NP900163F
Streptomyces
NCBITaxon:1883		 LOTUS DOI:10.1021/OL501179W
Streptomyces griseus
NCBITaxon:1911		 LOTUS DOI:10.1126/SCIENCE.108.2808.437-A

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000175 Streptomyces sp. YIM 56141
NCBITaxon:1211968 		CLUSTER_DEMONSTRATED genbank:JX014302.1

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

PRODUCERS & OCCURRENCE 1 producer (1 causal) 3 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT cycloheximide naturalproductmech:mibig-ab5ddd856a Alkaloids TARGETS & BIOACTIVITY 0 molecular targets 25 bioactivities · 0 graphs

Bioactivities 25

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

AssayResultTarget enzymeSource detail
7124-01: Inhibition of CD40 signaling in B cell lineageOTHER 0.393 uM; ACTIVENot recorded
pubchem.aid:1259332
assay
7124-01: Inhibition of CD40 signaling in B cell lineage
evidence
  • reference
    pubchem.aid:1259332
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1259332, deposited by Broad Institute; assay type Other. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
0.393
units
uM
activity class
ENZYME_INHIBITOR
7124-02: inhibition of TNFa signaling in B cell lineage, counterscreenOTHER 0.199 uM; ACTIVENot recorded
pubchem.aid:1259334
assay
7124-02: inhibition of TNFa signaling in B cell lineage, counterscreen
evidence
  • reference
    pubchem.aid:1259334
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1259334, deposited by Broad Institute; assay type Other. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
0.199
units
uM
activity class
ENZYME_INHIBITOR
7124-04: Celltiter Glo, Cytotoxicity assayOTHER 20 uM; INACTIVENot recorded
pubchem.aid:1259333
assay
7124-04: Celltiter Glo, Cytotoxicity assay
evidence
  • reference
    pubchem.aid:1259333
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1259333, deposited by Broad Institute; assay type Other. Source endpoint: AC50.
call
INACTIVE
measurement type
OTHER
value
20.0
units
uM
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 40 hourOTHER 19.4938 uM; ACTIVENot recorded
pubchem.aid:1224871
assay
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 40 hour
evidence
  • reference
    pubchem.aid:1224871
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1224871, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
19.4938
units
uM
activity class
CYTOTOXIC
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 40 hourOTHER 3.0107 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1224871
assay
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 40 hour
evidence
  • reference
    pubchem.aid:1224871
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1224871, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
3.0107
units
uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell PathologyOTHER 7.0795 uM; NOT_DETERMINEDNot 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
7.0795
units
uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell PathologyOTHER 7.0795 uM; NOT_DETERMINEDUniProtKB: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
7.0795
units
uM
target enzyme
UniProtKB:O14656
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.OTHER 0.4611 uM; NOT_DETERMINEDNot recorded
pubchem.aid:624296
assay
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.
evidence
  • reference
    pubchem.aid:624296
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624296, 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
0.4611
units
uM
Anti-Malarial Hsp90 Inhibitors Measured in Microorganism System Using Plate Reader - 2121-01_Inhibitor_Dose_CherryPick_ActivityOTHER 0.195 uM; ACTIVENot recorded
pubchem.aid:540268
assay
Anti-Malarial Hsp90 Inhibitors Measured in Microorganism System Using Plate Reader - 2121-01_Inhibitor_Dose_CherryPick_Activity
evidence
  • reference
    pubchem.aid:540268
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 540268, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50. Target accession XP_001348591 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
ACTIVE
measurement type
OTHER
value
0.195
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell lineOTHER 0.7422 uM; ACTIVENot recorded
pubchem.aid:2202236
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line
evidence
  • reference
    pubchem.aid:2202236
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202236, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.7422
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell lineOTHER 0.8327 uM; ACTIVENot recorded
pubchem.aid:2202237
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line
evidence
  • reference
    pubchem.aid:2202237
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202237, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.8327
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell lineOTHER 0.2633 uM; ACTIVENot recorded
pubchem.aid:2202234
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line
evidence
  • reference
    pubchem.aid:2202234
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202234, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.2633
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell lineOTHER 0.5254 uM; ACTIVENot recorded
pubchem.aid:2202233
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line
evidence
  • reference
    pubchem.aid:2202233
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202233, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.5254
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell lineOTHER 1.6616 uM; ACTIVENot recorded
pubchem.aid:2202232
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line
evidence
  • reference
    pubchem.aid:2202232
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202232, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
1.6616
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell lineOTHER 0.2955 uM; ACTIVENot recorded
pubchem.aid:2202231
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line
evidence
  • reference
    pubchem.aid:2202231
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202231, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.2955
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell lineOTHER 0.2633 uM; ACTIVENot recorded
pubchem.aid:2202235
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line
evidence
  • reference
    pubchem.aid:2202235
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202235, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.2633
units
uM
CMV-Luciferase Counterscreen for Inhibitors of ATXN expressionOTHER 2.8184 uM; ACTIVENot recorded
PMID:35787375
assay
CMV-Luciferase Counterscreen for Inhibitors of ATXN expression
evidence
  • reference
    PMID:35787375
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1745847, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.8184
units
uM
activity class
ENZYME_INHIBITOR
CMV-Luciferase Counterscreen for Inhibitors of ATXN expressionOTHER 2.8184 uM; ACTIVEUniProtKB:Q99700
PMID:35787375
assay
CMV-Luciferase Counterscreen for Inhibitors of ATXN expression
evidence
  • reference
    PMID:35787375
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1745847, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.8184
units
uM
target enzyme
UniProtKB:Q99700
activity class
ENZYME_INHIBITOR
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 0.0242 uM; ACTIVENot 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
0.0242
units
uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 0.0686 uM; ACTIVENot 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
0.0686
units
uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 0.1883 uM; ACTIVENot 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
0.1883
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 0.1212 uM; ACTIVENot 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
0.1212
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 1.7229 uM; ACTIVENot 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
1.7229
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 0.7498 uM; ACTIVENot 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
0.7498
units
uM
Cell Viability - LYMP1-002 - Assay at 16 hrOTHER 1.2589 uM; NOT_DETERMINEDNot recorded
pubchem.aid:948
assay
Cell Viability - LYMP1-002 - Assay at 16 hr
evidence
  • reference
    pubchem.aid:948
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 948, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
1.2589
units
uM
notes
935 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.

Explore across X-Mech

AntibioticMech (cycloheximide) ↗ MediaIngredientMech (naturalproductmech:mibig-ab5ddd856a) ↗ TaxonMech: Streptomyces sp. YIM 56141 (NCBITaxon:1211968) ↗ PathwayMech (mibig:BGC0000175) ↗

Provenance

Source conceptSourceVersion
BGC0000175MIBIG5

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