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CHEBI:138435 - bis(7)-tacrine

Default Structure
ChEBI IDCHEBI:138435
ChEBI Namebis(7)-tacrine
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:40503
Last Modified25 September 2017
SubmitterCharles Tapley Hoyt
DownloadsMolfile
FormulaC33H40N4
Net Charge0
Average Mass492.711
Monoisotopic Mass492.32530
SMILESc1ccc2c(NCCCCCCCNc3c4c(nc5ccccc35)CCCC4)c3c(nc2c1)CCCC3
InChIInChI=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)
InChIKeyITZOKHKOFJOBFS-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
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).
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:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
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  Source
B7TChEBI
bis(7)-tetrahydroaminacrineChEBI
heptylene-bis(tacrine)ChEBI
N,N'-bis(1,2,3,4-tetrahydro-9-acridinyl)-1,7-heptanediamineSUBMITTER
Manual XrefsDatabases
7828118ChemSpider
AA7PDBeChem
Registry NumbersSources
Reaxys:7608979Reaxys
Citations