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CHEBI:134547 - TOP-53

ChEBI IDCHEBI:134547
ChEBI NameTOP-53
Stars
DefinitionA 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.
Last Modified17 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC28H36N2O7
Net Charge0
Average Mass512.603
Monoisotopic Mass512.25225
SMILES[H][C@]12COC(=O)[C@]1([H])[C@H](c1cc(OC)c(O)c(OC)c1)c1cc3c(cc1[C@H]2CCN(C)CCN(C)C)OCO3
InChIInChI=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
InChIKeyKLCCMMSKRMSMKI-QVNMXXJYSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
TOP-53 (CHEBI:134547) has role antineoplastic agent (CHEBI:35610)
TOP-53 (CHEBI:134547) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
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)
TOP-53 (CHEBI:134547) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(5R,5aR,8aR,9S)-9-(2-{[2-(dimethylamino)ethyl](methyl)amino}ethyl)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Synonyms  Source
TOP 53ChEBI
4'-demethyl-4β-(2-{N-[2-(N',N'-dimethylamino)ethyl]-N-methylamino}ethyl)-4-desoxypodophyllotoxinChEBI
Registry NumbersSources
Reaxys:6377812Reaxys
CAS:148262-19-5ChemIDplus
Citations