CHEBI:64318 - ergotamine

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ChEBI Name ergotamine
ChEBI ID CHEBI:64318
Definition A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Colin Batchelor
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Formula C33H35N5O5
Net Charge 0
Average Mass 581.673
Monoisotopic Mass 581.26382
InChI InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
InChIKey XCGSFFUVFURLIX-VFGNJEKYSA-N
SMILES [H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O
Roles Classification
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ergotamine (CHEBI:64318) has role α-adrenergic agonist (CHEBI:35569)
ergotamine (CHEBI:64318) has role mycotoxin (CHEBI:25442)
ergotamine (CHEBI:64318) has role non-narcotic analgesic (CHEBI:35481)
ergotamine (CHEBI:64318) has role oxytocic (CHEBI:36063)
ergotamine (CHEBI:64318) has role serotonergic agonist (CHEBI:35941)
ergotamine (CHEBI:64318) has role vasoconstrictor agent (CHEBI:50514)
ergotamine (CHEBI:64318) is a peptide ergot alkaloid (CHEBI:25904)
ergotamine (CHEBI:64318) is conjugate base of ergotamine(1+) (CHEBI:190463)
Incoming ergotamine(1+) (CHEBI:190463) is conjugate acid of ergotamine (CHEBI:64318)
IUPAC Name
(5'α)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
INNs Sources
ergotamina ChemIDplus
ergotamine KEGG DRUG
ergotaminum ChemIDplus
Synonyms Sources
(5'α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione NIST Chemistry WebBook
12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione NIST Chemistry WebBook
12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione ChemIDplus
Ergotamin ChemIDplus
Gynergen ChemIDplus
Manual Xrefs Databases
1043 DrugCentral
7930 ChemSpider
C00001724 KNApSAcK
C07544 KEGG COMPOUND
D07906 KEGG DRUG
DB00696 DrugBank
Ergotamine Wikipedia
ERM PDBeChem
HMDB0014834 HMDB
View more database links
Registry Numbers Types Sources
113-15-5 CAS Registry Number KEGG DRUG
113-15-5 CAS Registry Number ChemIDplus
113-15-5 CAS Registry Number NIST Chemistry WebBook
78890 Beilstein Registry Number ChemIDplus
78890 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
11 April 2022