Teniposide

Details

• Internal ID: 84926f72-d7eb-4043-bfec-77abdc3dc356
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)CO[C@H](O7)C8=CC=CS8)O)O
• 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
• InChI Key: NRUKOCRGYNPUPR-QBPJDGROSA-N
• Popularity: 1,242 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₂O₁₃S
• Molecular Weight: 656.70 g/mol
• Exact Mass: 656.15636224 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 1.20

Synonyms

• 29767-20-2
• Vumon
• Vehem
• VM-26
• Teniposido
• NSC-122819
• VM26
• NSC 122819
• Epidophyllotoxin
• HSDB 6546
• VM 26
• DTXSID8023638
• 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside)
• 4'-Demethylepipodophyllotoxin-beta-D-thenylidine glucoside
• 957E6438QA
• 4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
• NSC122819
• (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• Demethyl Epipodophyllotoxin Thenylidine Glucoside
• CHEBI:75988
• Thenylidene Lignan
• (5S,5aR,8aR,9R)-5-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-(2)benzofuro(6,5-f)(1,3)benzodioxol-8-one
• RefChem:187844
• 4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucoside
• L01CB02
• DTXCID901508577
• (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
• (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
• (5R-(5Alpha,5a beta,8a alpha, 9beta(R*)))-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4,6-O-(2-thienylmethylene)-beta-D-glucopyranosyl)oxy)furo(3',4':6,7)-naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
• 249-831-2
• Teniposide (Vumon)
• Teniposidum [INN-Latin]
• Teniposido [INN-Spanish]
• C32H32O13S
• 5-[[(6R)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-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)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• Vee M-26
• Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
• Teniposide [USAN]
• MFCD00866516
• (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(2-thienyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
• CCRIS 2058
• EINECS 249-831-2
• 4'-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin
• Teniposide [USAN:INN:BAN]
• 4'-Demethyl-epipodophyllotoxin-beta-D-thenylidene-glucoside
• 4'-Dimethylepipodophyllotoxin-(4,6-O-2-thenylidene)-b-D-glucopyranoside
• UNII-957E6438QA
• Teniposide (Standard)
• Epipodophyllotoxin-beta-D-thenylidene-glucoside, 4'-demethyl-
• TENIPOSIDE [MI]
• TENIPOSIDE [INN]
• TENIPOSIDE [HSDB]
• TENIPOSIDE [IARC]
• TENIPOSIDE [VANDF]
• SCHEMBL3908
• TENIPOSIDE [MART.]
• 4'-Demethyl 1-O-(4,6-O,O-(2-thenylidene)-beta-D-glucopyranosyl)epipodophyllotoxin
• TENIPOSIDE [USP-RS]
• TENIPOSIDE [WHO-DD]
• (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-6-O-(2-thienylmethylene)-beta-D-glucopyranosyl)oxy)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
• CHEMBL452231
• GTPL6843
• orb1308336
• Teniposide - Bio-X trade mark
• SCHEMBL31499427
• TENIPOSIDE [ORANGE BOOK]
• 4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-2-THENYLIDENE-.BETA.-D-GLUCOPYRANOSIDE)
• GLXC-06579
• TENIPOSIDE [USP MONOGRAPH]
• BDBM50248198
• HY-13761R
• NSC758255
• s1787
• AKOS015896073
• CCG-270335
• CS-1366
• DB00444
• FT09381
• KS-5147
• NSC-758255
• BT164452
• 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-((R)-2-thienylmethylene)-beta-D-glucopyranosyl)oxy)-, (5R,5aR,8aR,9S)-
• 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)-beta-D-glucopyranosyl)-oxy)-, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
• HY-13761
• NS00069819
• AB01274729-01
• AB01274729_02
• EN300-7481406
• 767T202
• Q417555
• I06-2040
• BRD-K10362825-001-03-4
• -5-yl 4,6-O-(thiophen-2-ylmethylidene)-beta-D-glucopyranoside
• (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[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-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)-5,5a,8a,9-Tetrahydrofuro[3,4:6,7]Naphtho[2,3-d][1,3]Dioxol-6(8H)-One
• (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
• 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)-.BETA.-D-GLUCOPYRANOSYL)-OXY)-, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))
• 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-[(R)-2-thienylmethylene]-.beta.-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.46%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.49%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.79%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.43%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.19%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.55%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.28%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.14%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	90.90%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.86%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.50%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.77%	94.45%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.71%	96.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.16%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.51%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.88%	90.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.82%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.70%	99.15%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.18%	85.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 452548
• NPASS: NPC473803
• ChEMBL: CHEMBL452231