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29767-20-2 molecular structure
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(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 and InChIs

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

Cite this record

CBID:327 http://www.chembase.cn/molecule-327.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
29767-20-2
PubChem SID
160963790
46507536
PubChem CID
34698

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00444 external link
PubChem 34698 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.329948  H Acceptors 12 
H Donor LogD (pH = 5.5) 2.7839653 
LogD (pH = 7.4) 2.7789927  Log P 2.7840292 
Molar Refractivity 155.6095 cm3 Polarizability 62.344456 Å3
Polar Surface Area 160.83 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 2.78  LOG S -4.04 
Solubility (Water) 5.98e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
1.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00444 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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