α-ergocryptine
CHEBI:10276 EXACT SEEDED antiviralenzyme inhibitor
Ergotaman bearing hydroxy, isopropyl, and 2-methylpropyl groups at the 12', 2' and 5' positions, respectively, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid. Ergocryptine discussed in the literature prior to 1967, when β-ergocryptine was separated from α-ergocryptine, is now referred to as α-ergocryptine.
Structure
| Standard InChIKey | YDOTUXAWKBPQJW-NSLWYYNWSA-N |
|---|---|
| SMILES | CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O |
| Stereochemistry | fully defined |
| Cross-references | chembl:CHEMBL1403281, pubchem:134551 |
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 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 |
|---|---|---|---|
| Claviceps fusiformis NCBITaxon:40602 |
SOURCE_ASSERTION | mibig:BGC0001241 | DOI:10.1371/journal.pgen.1003323 |
Occurrences 10
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 |
|---|---|---|
| Festuca arundinacea NCBITaxon:4606 |
LOTUS | DOI:10.1021/JF00064A038 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1007/BF01937731 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1016/S0021-9673(98)00099-5 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1021/NP50036A010 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1021/NP50054A009 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1128/AEM.59.7.2029-2033.1993 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1139/V79-263 |
| Festuca rubra NCBITaxon:52153 |
LOTUS | DOI:10.1021/JF00064A038 |
| Claviceps grohii NCBITaxon:89176 |
LOTUS | DOI:10.1021/NP8001173 |
| Claviceps zizaniae NCBITaxon:89180 |
LOTUS | DOI:10.1021/NP010639W |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001241 | Claviceps fusiformis NCBITaxon:40602 |
CLUSTER_UNSTATED | genbank:JN186799.1 |
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 quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 0.0651 uM | pubchem.aid:624297 |
| Inhibitors of Regulator of G Protein Signaling (RGS) 4: qHTS | 56.2341 uM | pubchem.aid:504845 |
| Inhibitors of Secretory Acid Sphingomyelinase (S-ASM): qHTS | 31.6228 uM | pubchem.aid:504937 |
| Inhibitors of USP1/UAF1: Primary Screen | 17.7828 uM | pubchem.aid:743255 |
| Inhibitors of the vitamin D receptor (VDR): qHTS | 79.4328 uM | pubchem.aid:504847 |
| Nrf2 qHTS screen for inhibitors | 12.9953 uM | pubchem.aid:504444 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation | 2.9362 uM | pubchem.aid:504832 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 3.6964 uM | pubchem.aid:504834 |
| qHTS Assay for Iinhibitors of HIV-1 Budding by Blocking the Interaction of PTAP/TSG101 | 50.1187 uM | pubchem.aid:493005 |
| qHTS Assay for Iinhibitors of HIV-1 Budding by Blocking the Interaction of PTAP/TSG101: Hit Validation in TR assay | 0.3659 uM | pubchem.aid:651599 |
| qHTS Assay for Inhibitors of Hepatitis C Virus (HCV) | 11.2202 uM | pubchem.aid:651820 |
| qHTS Assay for Inhibitors of Histone Lysine Methyltransferase G9a | 6.3096 uM | pubchem.aid:504332 |
| qHTS Assay for Inhibitors of JMJD2A-Tudor Domain | 50.1187 uM | pubchem.aid:504339 |
| qHTS Assay for Inhibitors of Mammalian Selenoprotein Thioredoxin Reductase 1 (TrxR1): qHTS | 15.8489 uM | pubchem.aid:588453 |
| qHTS Assay for Inhibitors of RanGTP induced Rango (Ran-regulated importin-beta cargo) - Importin beta complex dissociation | 31.6228 uM | pubchem.aid:540253 |
| qHTS Assay for Inhibitors of RanGTP induced Rango (Ran-regulated importin-beta cargo) - Importin beta complex dissociation | 31.6228 uM | pubchem.aid:540253 |
| qHTS Assay for Inhibitors of RanGTP induced Rango (Ran-regulated importin-beta cargo) - Importin beta complex dissociation | 31.6228 uM | pubchem.aid:540253 |
| qHTS Assay for Inhibitors of Rango (Ran-regulated importin-beta cargo) - Importin beta complex formation | 100 uM | pubchem.aid:540263 |
| qHTS Assay for Inhibitors of Rango (Ran-regulated importin-beta cargo) - Importin beta complex formation | 100 uM | pubchem.aid:540263 |
| qHTS Assay for Inhibitors of Ubiquitin-specific Protease USP2a Using CHOP2 as the Reporter | 11.2202 uM | pubchem.aid:463254 |
| qHTS Assay for Substrates of Mammalian Selenoprotein Thioredoxin Reductase 1 (TrxR1): qHTS | 44.6684 uM | pubchem.aid:588456 |
| qHTS Assay for the Inhibitors of Human Flap endonuclease 1 (FEN1). | 12.5893 uM | pubchem.aid:588795 |
| qHTS Assay for the Inhibitors of Schistosoma Mansoni Peroxiredoxins | 5.6234 uM | pubchem.aid:485364 |
| qHTS Assay to Find Inhibitors of Pin1 | 44.6684 uM | pubchem.aid:504891 |
| qHTS Inhibitors of AmpC Beta-Lactamase (assay without detergent) | 39.8107 uM | pubchem.aid:485341 |
Open questions 1
name-disagreement — ChEBI calls this structure 'α-ergocryptine' and MIBiG calls it 'ergocryptine'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001241 | MIBIG | 4 |
| CHEBI:10276 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/ergocryptine.yaml, which is generated from the committed inventories. Neither is edited by hand.