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CHEBI:75988 - teniposide

ChEBI IDCHEBI:75988
ChEBI Nameteniposide
Stars
DefinitionA furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.
Secondary ChEBI IDCHEBI:9917
Last Modified19 January 2021
DownloadsMolfile
FormulaC32H32O13S
Net Charge0
Average Mass656.662
Monoisotopic Mass656.15636
SMILES[H][C@@]1(c2cccs2)OC[C@@]2([H])O[C@@H](O[C@@H]3c4cc5c(cc4[C@@H](c4cc(OC)c(O)c(OC)c4)[C@@]4([H])C(=O)OC[C@]34[H])OCO5)[C@H](O)[C@@H](O)[C@]2([H])O1
InChIInChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
InChIKeyNRUKOCRGYNPUPR-QBPJDGROSA-N
Wikipedia
Roles Classification
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)
teniposide (CHEBI:75988) has functional parent podophyllotoxin (CHEBI:50305)
teniposide (CHEBI:75988) has role antineoplastic agent (CHEBI:35610)
teniposide (CHEBI:75988) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
teniposide (CHEBI:75988) is a aromatic ether (CHEBI:35618)
teniposide (CHEBI:75988) is a cyclic acetal (CHEBI:59770)
teniposide (CHEBI:75988) is a furonaphthodioxole (CHEBI:50307)
teniposide (CHEBI:75988) is a monosaccharide derivative (CHEBI:63367)
teniposide (CHEBI:75988) is a phenols (CHEBI:33853)
teniposide (CHEBI:75988) is a thiophenes (CHEBI:26961)
teniposide (CHEBI:75988) is a β-D-glucoside (CHEBI:22798)
teniposide (CHEBI:75988) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(thiophen-2-ylmethylidene)-β-D-glucopyranoside
INNs  Source
teniposideKEGG DRUG
tenipósidoDrugBank
teniposidumDrugBank
téniposideWHO MedNet
Synonyms  Source
VM-26KEGG COMPOUND
HSDB 6546ChemIDplus
NSC-122819ChemIDplus
4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucosideChemIDplus
NSC 122819ChemIDplus
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)ChemIDplus
Brand Name  Source
VumonChemIDplus
Manual XrefsDatabases
C11153KEGG COMPOUND
9TPPDBeChem
D02698KEGG DRUG
DB00444DrugBank
HMDB0014587HMDB
TeniposideWikipedia
2590DrugCentral
CPD-16755MetaCyc
Registry NumbersSources
Reaxys:1417328Reaxys
CAS:29767-20-2KEGG COMPOUND
CAS:29767-20-2ChemIDplus
Citations