ergotamine

CHEBI:64318 EXACT SEEDED enzyme 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 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.

Mechanism & Biosynthesis Overview

Bioactivities 25

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

Explore across X-Mech

AntibioticMech (ergotamine) ↗ MediaIngredientMech (CHEBI:64318) ↗ TaxonMech: Claviceps fusiformis (NCBITaxon:40602) ↗ TaxonMech: Claviceps purpurea 20.1 (NCBITaxon:1111077) ↗ PathwayMech (mibig:BGC0001241) ↗ PathwayMech (mibig:BGC0002232) ↗

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.

Assay	Result	Target enzyme	Source detail
Confirmatory qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)	OTHER 0.8955 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1964105 assay Confirmatory qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) evidence reference pubchem.aid:1964105 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964105, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 0.8955 units uM
Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4)	OTHER 35.4813 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1845192 assay Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) evidence reference pubchem.aid:1845192 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1845192, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 35.4813 units uM
Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4)	OTHER 35.4813 uM; NOT_DETERMINED	UniProtKB:P36969	pubchem.aid:1845192 assay Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) evidence reference pubchem.aid:1845192 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1845192, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 35.4813 units uM target enzyme UniProtKB:P36969
Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)	OTHER 9.8843 uM; NOT_DETERMINED	UniProtKB:Q8JUX6	pubchem.aid:1964107 assay Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) evidence reference pubchem.aid:1964107 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964107, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 9.8843 units uM target enzyme UniProtKB:Q8JUX6
Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Endogenous NS2/3 peptide Counterscreen	OTHER 12.981 uM; ACTIVE	UniProtKB:Q8JUX6	pubchem.aid:1964103 assay Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Endogenous NS2/3 peptide Counterscreen evidence reference pubchem.aid:1964103 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964103, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 12.981 units uM target enzyme UniProtKB:Q8JUX6 activity class ENZYME_INHIBITOR
Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Full length NSP2 enzyme counterscreen (CHIKV-NSP2)	OTHER 2.5901 uM; NOT_DETERMINED	UniProtKB:Q8JUX6	pubchem.aid:1964101 assay Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Full length NSP2 enzyme counterscreen (CHIKV-NSP2) evidence reference pubchem.aid:1964101 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964101, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 2.5901 units uM target enzyme UniProtKB:Q8JUX6
Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Papain Counterscreen	OTHER 25.9005 uM; INACTIVE	UniProtKB:P00784	pubchem.aid:1964104 assay Selectivity profile for inhibitors of NSP2Pro chikungunya virus (CHIKV): Papain Counterscreen evidence reference pubchem.aid:1964104 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964104, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call INACTIVE measurement type OTHER value 25.9005 units uM target enzyme UniProtKB:P00784
Agonists at Human 5-Hydroxytryptamine receptor 5-HT1F	ACTIVE	Not recorded	PMID:8380639 assay Agonists at Human 5-Hydroxytryptamine receptor 5-HT1F evidence reference PMID:8380639 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624233, deposited by IUPHAR-DB; assay type Other. Target accession NP_000857 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A	ACTIVE	Not recorded	PMID:15322733 assay Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624235, deposited by IUPHAR-DB; assay type Other. Target accession NP_001159419 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B	ACTIVE	Not recorded	PMID:11104741 assay Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B evidence reference PMID:11104741 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624219, deposited by IUPHAR-DB; assay type Other. Target accession NP_000858 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B	ACTIVE	Not recorded	PMID:15322733 assay Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624219, deposited by IUPHAR-DB; assay type Other. Target accession NP_000858 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C	ACTIVE	Not recorded	PMID:15322733 assay Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624216, deposited by IUPHAR-DB; assay type Other. Target accession NP_001243690 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e	ACTIVE	Not recorded	PMID:1608964 assay Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e evidence reference PMID:1608964 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624230, deposited by IUPHAR-DB; assay type Other. Target accession NP_000856 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e	ACTIVE	Not recorded	PMID:8380639 assay Agonists at Human 5-Hydroxytryptamine receptor 5-ht1e evidence reference PMID:8380639 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624230, deposited by IUPHAR-DB; assay type Other. Target accession NP_000856 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Rat 5-Hydroxytryptamine receptor 5-HT1F	ACTIVE	Not recorded	PMID:8384716 assay Agonists at Rat 5-Hydroxytryptamine receptor 5-HT1F evidence reference PMID:8384716 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624227, deposited by IUPHAR-DB; assay type Other. Target accession NP_068629 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2A	ACTIVE	Not recorded	PMID:11104741 assay Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2A evidence reference PMID:11104741 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624234, deposited by IUPHAR-DB; assay type Other. Target accession NP_058950 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2C	ACTIVE	Not recorded	PMID:11104741 assay Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2C evidence reference PMID:11104741 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624214, deposited by IUPHAR-DB; assay type Other. Target accession NP_036897 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT1D receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:10715164 assay Human 5-HT1D receptor (5-Hydroxytryptamine receptors) evidence reference PMID:10715164 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346528, deposited by IUPHAR-DB; assay type Other. Target accession NP_000855 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT1F receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:8380639 assay Human 5-HT1F receptor (5-Hydroxytryptamine receptors) evidence reference PMID:8380639 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346739, deposited by IUPHAR-DB; assay type Other. Target accession NP_000857 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT2A receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:15322733 assay Human 5-HT2A receptor (5-Hydroxytryptamine receptors) evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1259419, deposited by IUPHAR-DB; assay type Other. Target accession NP_001159419 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT2B receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:11104741 assay Human 5-HT2B receptor (5-Hydroxytryptamine receptors) evidence reference PMID:11104741 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346867, deposited by IUPHAR-DB; assay type Other. Target accession NP_000858 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT2B receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:15322733 assay Human 5-HT2B receptor (5-Hydroxytryptamine receptors) evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346867, deposited by IUPHAR-DB; assay type Other. Target accession NP_000858 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT2C receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:15322733 assay Human 5-HT2C receptor (5-Hydroxytryptamine receptors) evidence reference PMID:15322733 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346893, deposited by IUPHAR-DB; assay type Other. Target accession NP_001243690 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT5A receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:7988681 assay Human 5-HT5A receptor (5-Hydroxytryptamine receptors) evidence reference PMID:7988681 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1345068, deposited by IUPHAR-DB; assay type Other. Target accession NP_076917 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE
Human 5-HT5A receptor (5-Hydroxytryptamine receptors)	ACTIVE	Not recorded	PMID:11343685 assay Human 5-HT5A receptor (5-Hydroxytryptamine receptors) evidence reference PMID:11343685 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1345068, deposited by IUPHAR-DB; assay type Other. Target accession NP_076917 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE notes 15 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.