ergotamine
CHEBI:64318 EXACT SEEDED enzyme inhibitor
A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.
Structure
| Standard InChIKey | XCGSFFUVFURLIX-VFGNJEKYSA-N |
|---|---|
| SMILES | C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C |
| Stereochemistry | fully defined |
| Cross-references | chembl:CHEMBL442, pubchem:8223 |
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, other, from MIBiG.
Producer organisms 2
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 |
| Claviceps purpurea 20.1 NCBITaxon:1111077 |
SOURCE_ASSERTION | mibig:BGC0002232 | DOI:10.1039/c4np00062e |
Occurrences 11
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 |
|---|---|---|
| Cenchrus echinatus NCBITaxon:173841 |
LOTUS | DOI:10.1021/NP50071A021 |
| Festuca arundinacea NCBITaxon:4606 |
LOTUS | DOI:10.1021/JF00064A038 |
| Festuca arundinacea NCBITaxon:4606 |
LOTUS | DOI:10.1021/JF00080A023 |
| Festuca pratensis NCBITaxon:4608 |
LOTUS | DOI:10.1016/S0021-9673(01)83714-6 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1016/S0021-9673(98)00099-5 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1128/AEM.59.7.2029-2033.1993 |
| Claviceps purpurea NCBITaxon:5111 |
LOTUS | DOI:10.1515/IUPAC.87.0589 |
| Festuca rubra NCBITaxon:52153 |
LOTUS | DOI:10.1021/JF00064A038 |
| Festuca rubra NCBITaxon:52153 |
LOTUS | DOI:10.1021/JF00080A023 |
| Festuca ovina NCBITaxon:98750 |
LOTUS | DOI:10.1016/S0021-9673(01)83714-6 |
| Claviceps fusiformis NCBITaxon:40602 |
LOTUS | DOI:10.1128/AEM.01040-07 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001241 | Claviceps fusiformis NCBITaxon:40602 |
CLUSTER_UNSTATED | genbank:JN186799.1 |
| mibig:BGC0002232 | Claviceps purpurea 20.1 NCBITaxon:1111077 |
CLUSTER_UNSTATED | genbank:CAGA01000020.1 |
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 |
|---|---|---|
| Confirmatory qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 0.8955 uM | pubchem.aid:1964105 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 35.4813 uM | pubchem.aid:1845192 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 35.4813 uM | pubchem.aid:1845192 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 9.8843 uM | pubchem.aid:1964107 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Endogenous NS2/3 peptide Counterscreen | 12.981 uM | pubchem.aid:1964103 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Full length NSP2 enzyme counterscreen (CHIKV-NSP2) | 2.5901 uM | pubchem.aid:1964101 |
| Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Papain Counterscreen | 25.9005 uM | pubchem.aid:1964104 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-HT1F | ACTIVE | PMID:8380639 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A | ACTIVE | PMID:15322733 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B | ACTIVE | PMID:11104741 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B | ACTIVE | PMID:15322733 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C | ACTIVE | PMID:15322733 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e | ACTIVE | PMID:1608964 |
| Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e | ACTIVE | PMID:8380639 |
| Agonists at Rat 5-Hydroxytryptamine receptor 5-HT1F | ACTIVE | PMID:8384716 |
| Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2A | ACTIVE | PMID:11104741 |
| Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2C | ACTIVE | PMID:11104741 |
| Human 5-HT1D receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:10715164 |
| Human 5-HT1F receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:8380639 |
| Human 5-HT2A receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:15322733 |
| Human 5-HT2B receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:11104741 |
| Human 5-HT2B receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:15322733 |
| Human 5-HT2C receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:15322733 |
| Human 5-HT5A receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:7988681 |
| Human 5-HT5A receptor (5-Hydroxytryptamine receptors) | ACTIVE | PMID:11343685 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0001241, BGC0002232. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001241 | MIBIG | 4 |
| BGC0002232 | MIBIG | 2 |
| CHEBI:64318 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/ergotamine.yaml, which is generated from the committed inventories. Neither is edited by hand.