ContaminantDB: Teniposide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:06:10 UTC

Update Date

2016-11-09 01:09:11 UTC

Accession Number

CHEM003673

Identification

Common Name

Teniposide

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 2A
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Antineoplastic Agent
Drug
Enzyme Inhibitor
Ester
Ether
Metabolite
Nucleic Acid Synthesis Inhibitor
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)	ChEBI
4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucoside	ChEBI
HSDB 6546	ChEBI
NSC 122819	ChEBI
NSC-122819	ChEBI
Teniposido	ChEBI
Teniposidum	ChEBI
VM-26	ChEBI
Vumon	ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-b-D-glucopyranoside)	Generator
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-β-D-glucopyranoside)	Generator
4'-Demethylepipodophyllotoxin-b-D-thenylidene glucoside	Generator
4'-Demethylepipodophyllotoxin-β-D-thenylidene glucoside	Generator
Bristol myers brand OF teniposide	HMDB
Bristol myers squibb brand OF teniposide	HMDB
Bristol-myers brand OF teniposide	HMDB
Bristol-myers squibb brand OF teniposide	HMDB
Demethyl epipodophyllotoxin thenylidine glucoside	HMDB
Teniposide, (5a alpha,9 alpha(s*))-isomer	HMDB
VM 26	HMDB

Chemical Formula

C₃₂H₃₂O₁₃S

Average Molecular Mass

656.654 g/mol

Monoisotopic Mass

656.156 g/mol

CAS Registry Number

29767-20-2

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[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Traditional Name

teniposide

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1

InChI Identifier

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

InChI Key

NRUKOCRGYNPUPR-PSZSYXFXSA-N

Chemical Taxonomy

Description

belongs to the class of inorganic compounds known as metalloid oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a metalloid.

Kingdom

Inorganic compounds

Super Class

Mixed metal/non-metal compounds

Class

Metalloid organides

Sub Class

Metalloid oxides

Direct Parent

Metalloid oxides

Alternative Parents

Substituents

Metalloid oxide
Inorganic oxide
Inorganic salt
Inorganic metalloid salt

Molecular Framework

Not Available

External Descriptors

silicon oxide (CHEBI:30563 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Teniposide Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	242-246°C
Boiling Point	Not Available
Solubility	5.98e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.78	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.61 m³·mol⁻¹	ChemAxon
Polarizability	65.8 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a71-5785097000-98bde989946936a415b9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Teniposide,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zgi-0028609000-2103fbbc9230d944f190	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0119500000-822a8a5e0ce6ead99756	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-2219200000-70925247141bc507a296	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a5a-0518009000-b551c2cfb3b192aa0c97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ot-1409121000-a632ab719b28e6760ca1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0532-3009000000-a2fcbe218ec09c074476	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kai-0069518000-4ca4220ba0f0b87931d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0029001000-8525d63245524aa711d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f80-0129000000-340326fd8e647fd49e25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000009000-60dafc658503bb6aca9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-1002019000-4cb4998458f9b7c40d68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9103042000-d52ca9fb9e8848a4e5d7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.

Metabolism

Route of 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. Half Life: 5 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (1)

Uses/Sources

Teniposide is used for the treatment of refractory acute lymphoblastic leukaemia

Minimum Risk Level

Not Available

Health Effects

Not Available