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ChemSpider 2D Image | Teniposide | C32H32O13S

Teniposide

  • Molecular FormulaC32H32O13S
  • Average mass656.654 Da
  • Monoisotopic mass656.156372 Da
  • ChemSpider ID398606

  • defined stereocentres - 10 of 10 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(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 [ACD/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-thienylmethylen)-β-D-glucopyranosid [German] [ACD/IUPAC Name]
4,6-O-(2-Thiénylméthylène)-β-D-glucopyranoside de (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-diméthoxyphényl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphto[2,3-d][1,3]dioxol-5-yle [French] [ACD/IUPAC Name]
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-β-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)- [ACD/Index Name]
Teniposide [USAN] [Wiki]
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
(5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-?-D-glucopyranosyl]oxy]-furo[3?,4?:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-?-D-glucopyranosyl]oxy]-furo[3’,4’:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-?-D-glucopyranosyl]oxy]-furo[3Õ,4Õ:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-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
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3836 [DBID]
957E6438QA [DBID]
AIDS001999 [DBID]
AIDS-001999 [DBID]
HSDB 6546 [DBID]
NSC 122819 [DBID]
NSC122819 [DBID]
NSC-122819 [DBID]
UNII:957E6438QA [DBID]
UNII-957E6438QA [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      L01CB02 Wikidata Q417555

    • Chemical Class:

      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 to poisomerase II binding. ChEBI CHEBI:75988

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13761
      Cell Cycle/DNA Damage; MedChem Express HY-13761
      Teniposide(VM-26) is a semisynthetic derivative of podophyllotoxin and are increasingly used in cancer medicine; causing breaks in DNA via an interaction with DNA topoisomerase II. MedChem Express
      Teniposide(VM-26) is a semisynthetic derivative of podophyllotoxin and are increasingly used in cancer medicine; causing breaks in DNA via an interaction with DNA topoisomerase II.; IC50 value:; Targe t: Topo II; Teniposide is a phase-specific cytotoxic drug acting in the late S and early G2 phases of the cell cycle. MedChem Express HY-13761
      Teniposide(VM-26) is a semisynthetic derivative of podophyllotoxin and are increasingly used in cancer medicine; causing breaks in DNA via an interaction with DNA topoisomerase II.;IC50 value:;Target: Topo II;Teniposide is a phase-specific cytotoxic drug acting in the late S and early G2 phases of the cell cycle. It appears to act by causing breaks in DNA via an interaction with DNA topoisomerase II or by the formation of free radicals. The number of DNA-topoisomerase-II covalent complexes stabilized by VM-26 in WEHI-3B D+ cells was greatly increased when cells were exposed simultaneously to VM-26 and novobiocin for 1 hr, but not when cells were treated with m-AMSA and novobiocin for the same period of time. MedChem Express HY-13761
      Topoisomerase MedChem Express HY-13761

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 864.3±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 131.6±3.0 kJ/mol
Flash Point: 476.5±34.3 °C
Index of Refraction: 1.697
Molar Refractivity: 158.3±0.4 cm3
#H bond acceptors: 13
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 2
ACD/LogP: 1.71
ACD/LogD (pH 5.5): 1.42
ACD/BCF (pH 5.5): 7.07
ACD/KOC (pH 5.5): 141.13
ACD/LogD (pH 7.4): 1.42
ACD/BCF (pH 7.4): 7.05
ACD/KOC (pH 7.4): 140.72
Polar Surface Area: 189 Å2
Polarizability: 62.8±0.5 10-24cm3
Surface Tension: 82.4±5.0 dyne/cm
Molar Volume: 410.9±5.0 cm3

Click to predict properties on the Chemicalize site


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