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 581.66150
Monoisotopic Mass 581.264
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@@]12Cc3c[nH]c4cccc(C1=C[C@H](CN2C)C(=O)N[C@]1(C)O[C@]2(O)N([C@@H](Cc5ccccc5)C(=O)N5CCC[C@@]25[H])C1=O)c34
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.
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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 serotonergic agonist (CHEBI:35941)
ergotamine (CHEBI:64318) has role vasoconstrictor agent (CHEBI:50514)
ergotamine (CHEBI:64318) is a peptide ergot alkaloid (CHEBI:25904)
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
Database Links Databases
1043 DrugCentral
C07544 KEGG COMPOUND
D07906 KEGG DRUG
DB00696 DrugBank
Ergotamine Wikipedia
View more database links
Registry Numbers Types Sources
113-15-5 CAS Registry Number ChemIDplus
113-15-5 CAS Registry Number KEGG DRUG
113-15-5 CAS Registry Number NIST Chemistry WebBook
78890 Reaxys Registry Number Reaxys
78890 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017