CHEBI:66667 - manzamine A

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ChEBI Name manzamine A
ChEBI ID CHEBI:66667
Definition An alkaloid of the class of β-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C36H44N4O
Net Charge 0
Average Mass 548.76080
Monoisotopic Mass 548.35151
InChI InChI=1S/C36H44N4O/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2/b4-1-,13-7-/t26-,30-,34+,35-,36-/m0/s1
InChIKey FUCSLKWLLSEMDQ-MKYGIPPKSA-N
SMILES [H][C@]12C[C@]34CN5CCCC\C=C/CC[C@](O)(C=C(c6nccc7c8ccccc8[nH]c67)[C@]3([H])CC5)[C@]4([H])N1CCCC\C=C/2
Metabolite of Species Details
Acanthostrongylophora (NCBI:txid178473) See: PubMed
Haliclona (NCBI:txid34490) Manzamine A was isolated as Hydrochloride salt(positive charge on pyrrolidinium nitrogen) See: DOI
Pachypellina (WORMS:167006) Manzamine A was isolated as Hydrochloride salt(positive charge on pyrrolidinium nitrogen) See: PubMed
Roles Classification
Biological Role(s): anti-HSV-1 agent
An anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
EC 2.7.11.26 (tau-protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of tau-protein kinase inhibitor (EC 2.7.11.26).
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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.
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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing manzamine A (CHEBI:66667) has role animal metabolite (CHEBI:75767)
manzamine A (CHEBI:66667) has role anti-HSV-1 agent (CHEBI:64953)
manzamine A (CHEBI:66667) has role antimalarial (CHEBI:38068)
manzamine A (CHEBI:66667) has role antineoplastic agent (CHEBI:35610)
manzamine A (CHEBI:66667) has role EC 2.7.11.26 (tau-protein kinase) inhibitor (CHEBI:91092)
manzamine A (CHEBI:66667) has role marine metabolite (CHEBI:76507)
manzamine A (CHEBI:66667) is a β-carbolines (CHEBI:60834)
manzamine A (CHEBI:66667) is a alkaloid (CHEBI:22315)
manzamine A (CHEBI:66667) is a isoquinolines (CHEBI:24922)
Incoming 6-hydroxymanzamine A (CHEBI:66668) has functional parent manzamine A (CHEBI:66667)
8-hydroxymanzamine A (CHEBI:66669) has functional parent manzamine A (CHEBI:66667)
IUPAC Name
(4aR,7S,7aR,13Z,14aR,15aR,18Z)-5-(9H-β-carbolin-1-yl)-4,4a,9,10,11,12,14a,15-octahydro-3H-7,2-oct[3]enoazocino[1',2':1,5]pyrrolo[2,3-i]isoquinolin-7(1H,7aH)-ol
Manual Xref Database
US2012289533 Patent
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Registry Numbers Types Sources
104196-68-1 CAS Registry Number ChemIDplus
4625288 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10817722 PubMed citation Europe PMC
17708655 PubMed citation Europe PMC
18520099 PubMed citation Europe PMC
20017491 PubMed citation Europe PMC
20352293 PubMed citation Europe PMC
20645244 PubMed citation Europe PMC
23039372 PubMed citation Europe PMC
8158160 PubMed citation Europe PMC
Last Modified
04 February 2016