9TP

(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)-beta-D-glucopyranoside

Created: 2013-07-01
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count78
Chiral Atom Count10
Bond Count85
Aromatic Bond Count17
2D diagram of 9TP
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Chemical Component Summary

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)-beta-D-glucopyranoside
SynonymsTeniposide
Systematic Name (OpenEye OEToolkits)(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-bis(oxidanyl)-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(3,5-dimethoxy-4-oxidanyl-phenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
FormulaC32 H32 O13 S
Molecular Weight656.654
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C1OCC8C1C(c2cc(OC)c(O)c(OC)c2)c4cc3OCOc3cc4C8OC6OC5COC(OC5C(O)C6O)c7sccc7
SMILESCACTVS3.385COc1cc(cc(OC)c1O)[CH]2[CH]3[CH](COC3=O)[CH](O[CH]4O[CH]5CO[CH](O[CH]5[CH](O)[CH]4O)c6sccc6)c7cc8OCOc8cc27
SMILESOpenEye OEToolkits1.7.6COc1cc(cc(c1O)OC)C2c3cc4c(cc3C(C5C2C(=O)OC5)OC6C(C(C7C(O6)COC(O7)c8cccs8)O)O)OCO4
Canonical SMILESCACTVS3.385 COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@H](O[C@H]5[C@H](O)[C@H]4O)c6sccc6)c7cc8OCOc8cc27
Canonical SMILESOpenEye OEToolkits1.7.6 COc1cc(cc(c1O)OC)[C@@H]2c3cc4c(cc3[C@H]([C@@H]5[C@@H]2C(=O)OC5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)CO[C@H](O7)c8cccs8)O)O)OCO4
InChIInChI1.03 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
InChIKeyInChI1.03 NRUKOCRGYNPUPR-QBPJDGROSA-N

Drug Info: DrugBank

DrugBank IDDB00444 
NameTeniposide
Groups approved
DescriptionTeniposide is a semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.
Synonyms
  • Teniposid
  • Téniposide
  • Teniposido
  • 4'-demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside)
  • Teniposidum
Brand Names
  • Teniposide
  • Vumon
IndicationTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Substrates
  • Carbohydrates
  • Cardiotoxic antineoplastic agents
ATC-CodeL01CB02
CAS number29767-20-2

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA topoisomerase 2-alphaMEVSPLQPVNENMQVNKIKKNEDAKKRLSVERIYQKKTQLEHILLRPDTY...unknowninhibitor
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknownsubstrate
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL452231
PubChem 452548
ChEMBL CHEMBL452231
CCDC/CSD KUXJUL