CHEBI:75988 - teniposide

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ChEBI Name teniposide
ChEBI ID CHEBI:75988
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9917
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Formula C32H32O13S
Net Charge 0
Average Mass 656.65400
Monoisotopic Mass 656.156
InChI InChI=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
InChIKey NRUKOCRGYNPUPR-PSZSYXFXSA-N
SMILES COc1cc(cc(OC)c1O)[C@H]1[C@@H]2[C@H](COC2=O)[C@H](O[C@@H]2O[C@@H]3COC(O[C@H]3[C@H](O)[C@H]2O)c2cccs2)c2cc3OCOc3cc12
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
teniposide (CHEBI:75988) is a γ-lactone (CHEBI:37581)
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)
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-(2-thienylmethylene)-β-D-glucopyranoside
INNs Sources
teniposide KEGG DRUG
téniposide WHO MedNet
tenipósido DrugBank
teniposidum DrugBank
Synonyms Sources
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside) ChemIDplus
4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucoside ChemIDplus
HSDB 6546 ChemIDplus
NSC 122819 ChemIDplus
NSC-122819 ChemIDplus
VM-26 KEGG COMPOUND
VM-26 KEGG COMPOUND
Brand Name Source
Vumon ChemIDplus
Database Links Databases
9TP PDBeChem
C11153 KEGG COMPOUND
D02698 KEGG DRUG
DB00444 DrugBank
HMDB0014587 HMDB
Teniposide Wikipedia
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Registry Numbers Types Sources
1417328 Reaxys Registry Number Reaxys
29767-20-2 CAS Registry Number KEGG COMPOUND
29767-20-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21430063 PubMed citation Europe PMC
21821840 PubMed citation Europe PMC
22644709 PubMed citation Europe PMC
22846410 PubMed citation Europe PMC
23266449 PubMed citation Europe PMC
23466610 PubMed citation Europe PMC
23679827 PubMed citation Europe PMC
23838380 PubMed citation Europe PMC
Last Modified
22 February 2017