aphidicolin
CHEBI:2766 EXACT SEEDED antiparasiticantiviralcytotoxicenzyme inhibitor
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 InChIKey | NOFOAYPPHIUXJR-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 |
| Stereochemistry | fully defined |
| Cross-references | npatlas: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.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| 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.
| Taxon | Source | Reference |
|---|---|---|
| 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
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| 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.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| High Throughput Screen to Identify Compounds that Suppress the Growth of Cells with a Deletion of the PTEN Tumor Suppressor - Dose Response | EC50 0.839 uM | pubchem.aid:1047 |
| High Throughput Screen to Identify Compounds that Suppress the Growth of Human Colon Tumor Cells Lacking Oncogenic Beta Catenin Expression - Dose Response | EC50 1.731 uM | pubchem.aid:1045 |
| Leishmania major promastigote EC50 determinations | EC50 0.136 uM | pubchem.aid:2008 |
| Luminescence Cell-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to BJeLR RAS-Dependent Fibroblast | EC50 28.62 uM | pubchem.aid:1936 |
| Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT RAS-Independent Fibroblast | EC50 38.639 uM | pubchem.aid:1933 |
| Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to BJ-TERT-LT-ST RAS-Independent Fibroblast | EC50 150 uM | pubchem.aid:1935 |
| Luminescence Cell-Based Dose Response HTS to Identify Compounds Cytotoxic to DRD Non-Viral Oncogenic Fibroblast | EC50 150 uM | pubchem.aid:1934 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 8.0538 uM | PMID:31515284 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 141.254 uM | pubchem.aid:1671190 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 141.254 uM | pubchem.aid:1671190 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation | 0.5221 uM | pubchem.aid:504832 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 0.5858 uM | pubchem.aid:504834 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 2.8403 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 2.8403 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 3.1868 uM | pubchem.aid:1645876 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 3.1868 uM | pubchem.aid:1645876 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 50.1187 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 50.1187 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 7.9433 uM | pubchem.aid:1645887 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 7.9433 uM | pubchem.aid:1645887 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 10 uM | pubchem.aid:1645882 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 10 uM | pubchem.aid:1645882 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 63.0957 uM | pubchem.aid:1645886 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 63.0957 uM | pubchem.aid:1645886 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 1.0139 uM | pubchem.aid:1963824 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:2766 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000676 | MIBIG | 5 |
| CHEBI:2766 | CHEBI | 3-star |
This page is generated from data/natural_products/terpenoids/aphidicolin.yaml, which is generated from the committed inventories. Neither is edited by hand.