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aphidicolin

CHEBI:2766 EXACT SEEDED antiparasiticantiviralcytotoxicenzyme inhibitor

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.

Structure

Standard InChIKeyNOFOAYPPHIUXJR-APNQCZIXSA-N
SMILES[H][C@]12C[C@]3([H])C[C@]1(CC[C@]3(O)CO)[C@@]1(C)CC[C@@H](O)[C@@](C)(CO)[C@]1([H])CC2
Stereochemistryfully defined
Cross-referencesnpatlas:NPA010945, pubchem:457964, chembl:CHEMBL29711

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.

TaxonBasisClusterEvidence
Phoma betae
NCBITaxon:1979465		 SOURCE_ASSERTION mibig:BGC0000676 PMID:14745177

Occurrences 24

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
Nigrospora sphaerica
NCBITaxon:114231		 LOTUS DOI:10.1055/S-0034-1368301
Pyrenula
NCBITaxon:146308		 LOTUS DOI:10.1021/NP500143K
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1016/0031-9422(88)80267-X
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1016/0031-9422(92)80164-A
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1016/S0031-9422(96)00713-3
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1021/NP200431K
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/C39870001492
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19730002841
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19840002751
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19840002755
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19850002705
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19880002009
Cephalosporium aphidicola
NCBITaxon:2231603		 LOTUS DOI:10.1039/P19920002079
Cephalosporium aphidicola
NCBITaxon:2231603		 CHEBI PMID:21812410
Tolypocladium inflatum
NCBITaxon:29910		 LOTUS DOI:10.1021/NP200431K
Tolypocladium inflatum
NCBITaxon:29910		 CHEBI PMID:21812410
Pleospora bjoerlingii
NCBITaxon:318712		 LOTUS DOI:10.1016/S0040-4020(99)00392-0
Pleospora bjoerlingii
NCBITaxon:318712		 LOTUS DOI:10.1080/00021369.1984.10866385
Pleospora bjoerlingii
NCBITaxon:318712		 LOTUS DOI:10.1271/BBB1961.48.1687
Pleospora bjoerlingii
NCBITaxon:318712		 LOTUS DOI:10.1271/BBB1961.53.299
Pleospora bjoerlingii
NCBITaxon:318712		 LOTUS DOI:10.3186/JJPHYTOPATH.51.219
Nigrospora oryzae
NCBITaxon:335854		 LOTUS DOI:10.1055/S-0034-1368301
Botrytis cinerea
NCBITaxon:40559		 LOTUS DOI:10.1021/ACS.JNATPROD.9B00705
Aspergillus oryzae
NCBITaxon:5062		 CHEBI PMID:29191129

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000676 Phoma betae
NCBITaxon:1979465 		CLUSTER_DEMONSTRATED genbank:AB114137.1

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 (0 causal) 24 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT aphidicolin CHEBI:2766 Terpenoids 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
High Throughput Screen to Identify Compounds that Suppress the Growth of Cells with a Deletion of the PTEN Tumor Suppressor - Dose ResponseEC50 0.839 uM; ACTIVENot recorded
pubchem.aid:1047
assay
High Throughput Screen to Identify Compounds that Suppress the Growth of Cells with a Deletion of the PTEN Tumor Suppressor - Dose Response
evidence
  • reference
    pubchem.aid:1047
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1047, deposited by SRMLSC; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
0.839
units
uM
activity class
CYTOTOXIC
High Throughput Screen to Identify Compounds that Suppress the Growth of Human Colon Tumor Cells Lacking Oncogenic Beta Catenin Expression - Dose ResponseEC50 1.731 uM; ACTIVENot recorded
pubchem.aid:1045
assay
High Throughput Screen to Identify Compounds that Suppress the Growth of Human Colon Tumor Cells Lacking Oncogenic Beta Catenin Expression - Dose Response
evidence
  • reference
    pubchem.aid:1045
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1045, deposited by SRMLSC; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
1.731
units
uM
activity class
CYTOTOXIC
Leishmania major promastigote EC50 determinationsEC50 0.136 uM; ACTIVENot recorded
pubchem.aid:2008
assay
Leishmania major promastigote EC50 determinations
evidence
  • reference
    pubchem.aid:2008
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2008, deposited by University of Pittsburgh Molecular Library Screening Center; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
0.136
units
uM
activity class
ANTIPARASITIC
Luminescence Cell-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to BJeLR RAS-Dependent FibroblastEC50 28.62 uM; ACTIVENot recorded
pubchem.aid:1936
assay
Luminescence Cell-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to BJeLR RAS-Dependent Fibroblast
evidence
  • reference
    pubchem.aid:1936
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1936, deposited by Broad Institute; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
28.62
units
uM
activity class
CYTOTOXIC
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT RAS-Independent FibroblastEC50 38.639 uM; ACTIVENot recorded
pubchem.aid:1933
assay
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT RAS-Independent Fibroblast
evidence
  • reference
    pubchem.aid:1933
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1933, deposited by Broad Institute; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
38.639
units
uM
activity class
CYTOTOXIC
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT-LT-ST RAS-Independent FibroblastEC50 150 uM; INACTIVENot recorded
pubchem.aid:1935
assay
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT-LT-ST RAS-Independent Fibroblast
evidence
  • reference
    pubchem.aid:1935
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1935, deposited by Broad Institute; assay type Confirmatory.
call
INACTIVE
measurement type
EC50
value
150.0
units
uM
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to DRD Non-Viral Oncogenic FibroblastEC50 150 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1934
assay
Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to DRD Non-Viral Oncogenic Fibroblast
evidence
  • reference
    pubchem.aid:1934
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1934, deposited by Broad Institute; assay type Confirmatory. Source outcome: Inconclusive.
call
NOT_DETERMINED
measurement type
EC50
value
150.0
units
uM
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screenOTHER 8.0538 uM; NOT_DETERMINEDNot recorded
PMID:31515284
assay
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen
evidence
  • reference
    PMID:31515284
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346987, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
8.0538
units
uM
Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2OTHER 141.254 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671190
assay
Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2
evidence
  • reference
    pubchem.aid:1671190
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671190, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
141.254
units
uM
Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2OTHER 141.254 uM; NOT_DETERMINEDUniProtKB:P18054
pubchem.aid:1671190
assay
Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2
evidence
  • reference
    pubchem.aid:1671190
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671190, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
141.254
units
uM
target enzyme
UniProtKB:P18054
Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubationOTHER 0.5221 uM; ACTIVENot recorded
pubchem.aid:504832
assay
Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation
evidence
  • reference
    pubchem.aid:504832
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 504832, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.5221
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubationOTHER 0.5858 uM; ACTIVENot recorded
pubchem.aid:504834
assay
Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation
evidence
  • reference
    pubchem.aid:504834
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 504834, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.5858
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)OTHER 2.8403 uM; ACTIVENot recorded
pubchem.aid:1645877
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)
evidence
  • reference
    pubchem.aid:1645877
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645877, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.8403
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)OTHER 2.8403 uM; ACTIVEUniProtKB:O96028
pubchem.aid:1645877
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)
evidence
  • reference
    pubchem.aid:1645877
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645877, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.8403
units
uM
target enzyme
UniProtKB:O96028
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)OTHER 3.1868 uM; ACTIVENot recorded
pubchem.aid:1645876
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)
evidence
  • reference
    pubchem.aid:1645876
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645876, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.1868
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)OTHER 3.1868 uM; ACTIVEUniProtKB:O96028
pubchem.aid:1645876
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)
evidence
  • reference
    pubchem.aid:1645876
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645876, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.1868
units
uM
target enzyme
UniProtKB:O96028
activity class
ENZYME_INHIBITOR
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)OTHER 50.1187 uM; INACTIVENot recorded
pubchem.aid:1645883
assay
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)
evidence
  • reference
    pubchem.aid:1645883
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645883, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
50.1187
units
uM
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)OTHER 50.1187 uM; INACTIVEUniProtKB:O95398
pubchem.aid:1645883
assay
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)
evidence
  • reference
    pubchem.aid:1645883
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645883, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
50.1187
units
uM
target enzyme
UniProtKB:O95398
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 7.9433 uM; INACTIVENot recorded
pubchem.aid:1645887
assay
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645887
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645887, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
7.9433
units
uM
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 7.9433 uM; INACTIVEUniProtKB:Q8WZA2
pubchem.aid:1645887
assay
Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645887
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645887, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
7.9433
units
uM
target enzyme
UniProtKB:Q8WZA2
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)OTHER 10 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1645882
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)
evidence
  • reference
    pubchem.aid:1645882
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645882, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
10.0
units
uM
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)OTHER 10 uM; NOT_DETERMINEDUniProtKB:O95398
pubchem.aid:1645882
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1)
evidence
  • reference
    pubchem.aid:1645882
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645882, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
10.0
units
uM
target enzyme
UniProtKB:O95398
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 63.0957 uM; ACTIVENot recorded
pubchem.aid:1645886
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645886
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645886, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
63.0957
units
uM
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 63.0957 uM; ACTIVEUniProtKB:Q8WZA2
pubchem.aid:1645886
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645886
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645886, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
63.0957
units
uM
target enzyme
UniProtKB:Q8WZA2
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cellsOTHER 1.0139 uM; ACTIVENot recorded
pubchem.aid:1963824
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells
evidence
  • reference
    pubchem.aid:1963824
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963824, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
1.0139
units
uM
notes
46 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (aphidicolin) ↗ MediaIngredientMech (CHEBI:2766) ↗ TaxonMech: Phoma betae (NCBITaxon:1979465) ↗ PathwayMech (mibig:BGC0000676) ↗

Provenance

Source conceptSourceVersion
BGC0000676MIBIG5
CHEBI:2766CHEBI3-star

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