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 656.660
Monoisotopic Mass 656.15636
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-QBPJDGROSA-N
SMILES [H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=C(C=C3OCOC3=C1)[C@H]2O[C@@H]1O[C@]2([H])CO[C@]([H])(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1
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-(thiophen-2-ylmethylidene)-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
VM26 KEGG COMPOUND
Brand Name Source
Vumon ChemIDplus
Manual Xrefs Databases
2590 DrugCentral
9TP PDBeChem
C11153 KEGG COMPOUND
CPD-16755 MetaCyc
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
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Last Modified
19 January 2021