CHEBI:134547 - TOP-53

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ChEBI Name TOP-53
Definition A furonaphthodioxole that is 4'-demethyldeoxypodophyllotoxin which is substituted at position 4 of the C-ring by a 2-{[2-(dimethylamino)ethyl](methyl)amino}ethyl group. While structurally related to etoposide, TOP-53 is significantly more toxic to non-small cell lung cancer cells, more active at generating chromosomal breaks, and displays improved cellular uptake and pharmacokinetics in animal lung tissues.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H36N2O7
Net Charge 0
Average Mass 512.596
Monoisotopic Mass 512.25225
InChI InChI=1S/C28H36N2O7/c1-29(2)8-9-30(3)7-6-17-18-12-21-22(37-15-36-21)13-19(18)25(26-20(17)14-35-28(26)32)16-10-23(33-4)27(31)24(11-16)34-5/h10-13,17,20,25-26,31H,6-9,14-15H2,1-5H3/t17-,20-,25-,26+/m1/s1
SMILES C12=CC3=C(C=C1[C@H]([C@@]4([C@@]([C@@H]2CCN(CCN(C)C)C)(COC4=O)[H])[H])C=5C=C(C(=C(C5)OC)O)OC)OCO3
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 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing TOP-53 (CHEBI:134547) has role antineoplastic agent (CHEBI:35610)
TOP-53 (CHEBI:134547) has role EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
TOP-53 (CHEBI:134547) is a γ-lactone (CHEBI:37581)
TOP-53 (CHEBI:134547) is a furonaphthodioxole (CHEBI:50307)
TOP-53 (CHEBI:134547) is a organic heterotetracyclic compound (CHEBI:38163)
TOP-53 (CHEBI:134547) is a phenols (CHEBI:33853)
TOP-53 (CHEBI:134547) is a tertiary amino compound (CHEBI:50996)
Synonyms Sources
4'-demethyl-4β-(2-{N-[2-(N',N'-dimethylamino)ethyl]-N-methylamino}ethyl)-4-desoxypodophyllotoxin ChEBI
Registry Numbers Types Sources
148262-19-5 CAS Registry Number ChemIDplus
6377812 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11106259 PubMed citation Europe PMC
11170388 PubMed citation Europe PMC
12081147 PubMed citation Europe PMC
15892669 PubMed citation Europe PMC
15992351 PubMed citation Europe PMC
24827545 PubMed citation Europe PMC
8665518 PubMed citation Europe PMC
9106054 PubMed citation Europe PMC
Last Modified
17 February 2017