(10R,11R,15R,16S)-16-{[(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[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

• ChemBase ID: 327
• Molecular Formular: C32H32O13S
• Molecular Mass: 656.65368
• Monoisotopic Mass: 656.15636208
• SMILES: s1c(C2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@H]4[C@@H]5[C@@H]([C@@H](c6c4cc4OCOc4c6)c4cc(OC)c(O)c(OC)c4)C(=O)OC5)O[C@@H]3CO2)ccc1
• Canonical SMILES: COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@H]1O)O)c1cccs1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R,15R,16S)-16-{[(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[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
• IUPAC Traditional name: (10R,11R,15R,16S)-16-{[(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[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
• Brand Name: Vee M-26; Veham-Sandoz; Vehem; Vumon
• Synonyms: Teniposido [INN-Spanish]; Teniposidum [INN-Latin]; Teniposide

Database IDs

• CAS Number: 29767-20-2
• PubChem SID: 160963790; 46507536
• PubChem CID: 34698

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.329948
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 2.7839653
• LogD (pH = 7.4): 2.7789927
• Log P: 2.7840292
• Molar Refractivity: 155.6095 cm^3
• Polarizability: 62.344456 Å^3
• Polar Surface Area: 160.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.78
• LOG S: -4.04
• Solubility (Water): 5.98e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.5

DETAILS

DrugBank - DB00444

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: Teniposide is used for the treatment of refractory acute lymphoblastic leukaemia
• Pharmacology: Teniposide is a phase-specific cytotoxic drug, acting in the late S or early G 2 phase of the cell cycle, thus preventing cells from entering mitosis. Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA: protein cross-links.
• Affected Organisms: Humans and other mammals
• Half Life: 5 hours
• Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose.
• Clearance: * 10.3 mL/min/m2
• External Links: Wikipedia; RxList; Drugs.com