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CHEBI:138435 - bis(7)-tacrine

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:
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.
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
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
N,N'-bis(1,2,3,4-tetrahydro-9-acridinyl)-1,7-heptanediamineSUBMITTER
heptylene-bis(tacrine)ChEBI
B7TChEBI
bis(7)-tetrahydroaminacrineChEBI
Manual XrefsDatabases
AA7PDBeChem
7828118ChemSpider
Registry NumbersSources
Reaxys:7608979Reaxys
Citations