CHEBI:4781 - emetine

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ChEBI Name emetine
ChEBI ID CHEBI:4781
Definition A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C29H40N2O4
Net Charge 0
Average Mass 480.63898
Monoisotopic Mass 480.29881
InChI InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1
InChIKey AUVVAXYIELKVAI-CKBKHPSWSA-N
SMILES [H][C@]1(C[C@@]2([H])NCCc3cc(OC)c(OC)cc23)C[C@]2([H])N(CCc3cc(OC)c(OC)cc23)C[C@@H]1CC
Metabolite of Species Details
Carapichea ipecacuanha (NCBI:txid77880) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
antiviral agent
A substance that destroys or inhibits replication of viruses.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
autophagy inhibitor
Any compound that inhibits the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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): emetic
Any agent that induces nausea and vomiting.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
expectorant
Compounds that are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing. Compare with mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration, and antitussives, which suppress the cough reflex.
antiamoebic agent
An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
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ChEBI Ontology
Outgoing emetine (CHEBI:4781) has functional parent cephaeline (CHEBI:3533)
emetine (CHEBI:4781) has parent hydride emetan (CHEBI:36380)
emetine (CHEBI:4781) has role antiamoebic agent (CHEBI:171664)
emetine (CHEBI:4781) has role anticoronaviral agent (CHEBI:149553)
emetine (CHEBI:4781) has role antiinfective agent (CHEBI:35441)
emetine (CHEBI:4781) has role antimalarial (CHEBI:38068)
emetine (CHEBI:4781) has role antineoplastic agent (CHEBI:35610)
emetine (CHEBI:4781) has role antiprotozoal drug (CHEBI:35820)
emetine (CHEBI:4781) has role antiviral agent (CHEBI:22587)
emetine (CHEBI:4781) has role autophagy inhibitor (CHEBI:88230)
emetine (CHEBI:4781) has role emetic (CHEBI:149552)
emetine (CHEBI:4781) has role expectorant (CHEBI:77035)
emetine (CHEBI:4781) has role plant metabolite (CHEBI:76924)
emetine (CHEBI:4781) has role protein synthesis inhibitor (CHEBI:48001)
emetine (CHEBI:4781) is a isoquinoline alkaloid (CHEBI:24921)
emetine (CHEBI:4781) is a pyridoisoquinoline (CHEBI:61692)
emetine (CHEBI:4781) is conjugate base of emetine(2+) (CHEBI:149548)
Incoming emetamine (CHEBI:4780) has functional parent emetine (CHEBI:4781)
emetine(2+) (CHEBI:149548) is conjugate acid of emetine (CHEBI:4781)
IUPAC Name
6',7',10,11-tetramethoxyemetan
Synonyms Sources
cephaeline methyl ether ChemIDplus
cephaline-O-methyl ether ChemIDplus
Emetan NIST Chemistry WebBook
Emetin ChemIDplus
Emetine KEGG COMPOUND
methyl cephaeline ChemIDplus
Manual Xrefs Databases
1001 DrugCentral
C00001849 KNApSAcK
C09421 KEGG COMPOUND
CPD-14817 MetaCyc
DB13393 DrugBank
Emetine Wikipedia
LSM-2041 LINCS
View more database links
Registry Numbers Types Sources
100834 Reaxys Registry Number Reaxys
100834 Beilstein Registry Number Beilstein
483-18-1 CAS Registry Number NIST Chemistry WebBook
483-18-1 CAS Registry Number ChemIDplus
6253162 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
14119536 PubMed citation Europe PMC
16109351 PubMed citation Europe PMC
17094176 PubMed citation Europe PMC
19227966 PubMed citation Europe PMC
29872540 PubMed citation Europe PMC
31436297 PubMed citation Europe PMC
31533472 PubMed citation Europe PMC
31734270 PubMed citation Europe PMC
31775307 PubMed citation Europe PMC
31964796 PubMed citation Europe PMC
32245264 PubMed citation Europe PMC
32251767 PubMed citation Europe PMC
Last Modified
28 April 2021