CHEBI:138435 - bis(7)-tacrine

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ChEBI Name bis(7)-tacrine
ChEBI ID CHEBI:138435
Definition A secondary amino compound consisting of two molecules of tacrine that are linked together through their exocyclic amino groups by a heptane-1,7-diyl chain. Bis(7)-tacrine is an acetylcholinesterase (AChE)inhibitor (IC50 0.40 nM, >1,000 times more potent than tacrine). It has also been found to protect against H2O2 -induced apoptosis in rat pheochromocytoma cells.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Charles Tapley Hoyt
Secondary ChEBI IDs CHEBI:40503
Supplier Information
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Formula C33H40N4
Net Charge 0
Average Mass 492.699
Monoisotopic Mass 492.32530
InChI InChI=1S/C33H40N4/c1(2-12-22-34-32-24-14-4-8-18-28(24)36-29-19-9-5-15-25(29)32)3-13-23-35-33-26-16-6-10-20-30(26)37-31-21-11-7-17-27(31)33/h4,6,8,10,14,16,18,20H,1-3,5,7,9,11-13,15,17,19,21-23H2,(H,34,36)(H,35,37)
InChIKey ITZOKHKOFJOBFS-UHFFFAOYSA-N
SMILES C(CCCNC=1C2=CC=CC=C2N=C3CCCCC31)CCCNC=4C5=CC=CC=C5N=C6CCCCC64
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bis(7)-tacrine (CHEBI:138435) has functional parent tacrine (CHEBI:45980)
bis(7)-tacrine (CHEBI:138435) has role apoptosis inhibitor (CHEBI:68494)
bis(7)-tacrine (CHEBI:138435) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
bis(7)-tacrine (CHEBI:138435) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
bis(7)-tacrine (CHEBI:138435) has role neuroprotective agent (CHEBI:63726)
bis(7)-tacrine (CHEBI:138435) is a secondary amino compound (CHEBI:50995)
IUPAC Name
N,N'-di(1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine
Synonyms Sources
B7T ChEBI
bis(7)-tetrahydroaminacrine ChEBI
heptylene-bis(tacrine) ChEBI
N,N'-bis(1,2,3,4-tetrahydro-9-acridinyl)-1,7-heptanediamine SUBMITTER
Manual Xrefs Databases
7828118 Chemspider accession
AA7 PDBeChem
View more database links
Registry Number Type Source
7608979 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10208549 PubMed citation SUBMITTER
10452094 PubMed citation SUBMITTER
16543809 PubMed citation Europe PMC
17449090 PubMed citation Europe PMC
17530875 PubMed citation Europe PMC
19393253 PubMed citation Europe PMC
20043893 PubMed citation Europe PMC
20199668 PubMed citation Europe PMC
20486153 PubMed citation Europe PMC
21535411 PubMed citation Europe PMC
22330749 PubMed citation Europe PMC
22553626 PubMed citation Europe PMC
23832279 PubMed citation Europe PMC
26043757 PubMed citation Europe PMC
28294041 PubMed citation Europe PMC
28571743 PubMed citation Europe PMC
Last Modified
25 September 2017
General Comment
2017-09-25 Links to ChEMBL are created automatically based on matching structures. The links are currently created every month (normally on the first day of each month), so there will be a period (between 1 day and 1 month) after the initial entry is visible on the ChEBI website before the links appear (in the Automatic Xrefs tab).
 
Submitter Remark
2017-09-18 20:54:54.0 Charles Tapley Hoyt Also referenced as CHEMBL32823 referenced: https://www.ebi.ac.uk/chembl/compound/inspect/CHEMBL32823. I'm surprised there's no cross-reference type for ChEMBL