CAS 518-28-5|CAS 477-47-4|(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one|condylox|(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-...

基本信息

化学结构

分子式

C₂₂H₂₂O₈

分子量

414.40528

精确质量

414.13146766

电荷

InChI

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

InChIKey

YJGVMLPVUAXIQN-XVVDYKMHSA-N

Canonic Smiles

COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O

Isomeric Smiles

O1C[C@H]2[C@@H]([C@@H](c3c([C@@H]2O)cc2OCOc2c3)c2cc(OC)c(OC)c(OC)c2)C1=O

计算属性

JChem

LogD (pH = 7.4)

1.62

LogD (pH = 5.5)

1.62

Log P

1.62

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

13.40

极化表面积

92.68

极化性

41.81

摩尔折射率

103.90

LOG S

-3.62

数据来源

名称和标识

别名

(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONEPodofiloxPodophyllinic acid lactonePodophyllotoxin(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-onePodophyllotoxin(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-oneNSC 24818(-)-PodophyllotoxinPodofiloxCondylineCondyloxWarticonPodofiloxPodophyllinic acid lactonePodophyllotoxin(-)-podophyllotoxinpodophyllotoxinPodofilox9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONEPPT

IUPAC传统名

condylox podofilox (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

IUPAC标准名

(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-12-one

商标名

Podophyllotoxin 7PodophyllotoxinCondylox

API名称

Podophyllotoxin

名称和标识

数据登录号

化合物性质

产品相关信息

纯度

≥98%

95%

≥98.0% (HPLC)

Empirical Formula (Hill Notation)

C22H22O8

质检报告

下载链接

生物来源

Isol. from Podophyllum emodi, Diphylleia grayi and others

Cytostatic

药理学性质

生物活性机理

Reported to bind to tubulin

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

化合物性质

分子相关蛋白质

PDB Bank

1SA1

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB01179

Drug Groups

approved

Description

A lignan (lignans) found in podophyllin resin from the roots of podophyllum plants. It is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. It is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives. [PubChem]

Indication

For treatment of external genital warts (Condyloma acuminatum).

Pharmacology

Podofilox, also called podophyllotoxin, is a purer and more stable form of podophyllin in which only the biologically active portion of the compound is present. Podofilox is used to remove certain types of warts on the outside skin of the genital areas.

Affected Organisms

Condyloma acuminatum

Absorption

Topical application of 0.05 mL of 0.5% podofilox solution to external genitalia did not result in detectable serum levels. Applications of 0.1 to 1.5 mL resulted in peak serum levels of 1 to 17 ng/mL one to two hours after application.

Half Life

1.0 to 4.5 hours.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

DB08417

Drug information: experimental

Sigma Aldrich

P4405

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
100 mg in glass bottle
50 mg in poly bottle

858447

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
1 g in glass bottle
100 mg in glass bottle

81125

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
Other Notes
Inhibitor of microtubule assembly. Useful tool for tubulin studies1,2,3

TRC

P681000

Skin treatment for genital warts caused by some types of HPVs.

ChEBI

CHEBI:50305

An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts.

描述信息

参考文献

PubChem文献

数据源提供

• Gupta, R.S.; Cancer Research, 43, 505 (1983a)

• Kelly, M.G. & Hartwell, J.L.; J. of the Nat'l Cancer Inst., 14, 967 (1954)

• Gupta, R.S.; Somatic Cell Genetics, 7, 59 (1954)

• Duffield, A.M., J. Het. Chem., 1967, 4, 16, (ms)

• Nadkarni, M.V. et al., J.A.C.S., 1953, 75, 1308, (isol, derivs)

• Macdonald, D.I. et al., J.O.C., 1986, 51, 4749, (synth)

• Hartwell, J.L. et al., J.A.C.S., 1951, 73, 2909, (isol)

• Kamil, W.M. et al., Phytochemistry, 1986, 25, 2093, (biosynth)

• Jones, D.W. et al., Chem. Comm., 1987, 1797; 1989, 1370, (synth)

• Forsey, S.P. et al., J.O.C., 1989, 54, 4280, (synth)

• Wichers, H.J. et al., Phytochemistry, 1991, 30, 3601, (biosynth)

• Pelter, A. et al., Tetrahedron, 1994, 50, 10829, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1304A, (nmr)

• Stoll, A. et al., J.A.C.S., 1954, 76, 3103, (glucoside)

• Inamori, Y. et al., Chem. Pharm. Bull., 1986, 34, 3928, (props)

• Thurston, L.S. et al., J. Med. Chem., 1989, 32, 604, (pharmacol)

• Andersen, K.V. et al., J.C.S. Perkin 2, 1990, 1871, (cryst struct)

• Ayres, D.C. et al., Lignans, Chem. Biol. and Clinical Props., Cambridge, 1990, (rev)

• Sackett, D.L., Pharmacol. Ther., 1993, 59, 163, (rev)

• Andrews, R.C. et al., J.A.C.S., 1988, 110, 7854, (synth)

• Macdonald, D.I. et al., J.O.C., 1988, 43, 3663, (synth)

• Kaneko, T. et al., Tet. Lett., 1987, 28, 517, (synth)

• Ward, R.S., Synthesis, 1992, 719, (rev, synth, bibl)

• Jackson, D.E. et al., Phytochemistry, 1984, 23, 1029; 1037, (biosynth)

• Puri, H.S., Planta Med., 1988, 54, 269, (isol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 765

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 320A, (ir)

• Vyas, D.M. et al., Tet. Lett., 1986, 27, 3099, (synth)

• Van Speybroeck, R. et al., Tetrahedron, 1991, 47, 4675, (synth)

• Schrecker, A.W. et al., J.O.C., 1956, 21, 288; 381, (props, abs config)

• Gensler, W.J. et al., J.A.C.S., 1962, 84, 1748, (synth)

• Gensler, W.J. et al., J.O.C., 1966, 31, 3224, (synth)

• Ayres, D.C. et al., J.C.S. Perkin 1, 1972, 1343, (pmr)

• Petcher, T.J. et al., J.C.S. Perkin 2, 1973, 288, (cryst struct)

• Van der Eycken, J. et al., Tetrahedron, 1986, 42, 4297, (synth)

• Lim, Y.-H. et al., Arch. Pharmacal Res., 1999, 22, 208-212, (Angeloylpodophyllotoxin)

• Canel, C. et al., Phytochemistry, 2000, 54, 115-120, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EBB600

• Del Corral, J.M.M. et al., J. Nat. Prod., 1995, 58, 870, (synth, pmr, cmr)

• Zhao, C. et al., Chem. Pharm. Bull., 2001, 49, 773-775, (Isopodophyllotoxin 7-gentiobioside)

• Bush, E.J. et al., J.C.S. Perkin 1, 1996, 151, (synth)

• Berkowitz, D.B. et al., J.O.C., 2000, 65, 847-860, (synth, bibl)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

IUPAC标准名

商标名

Podophyllotoxin 7PodophyllotoxinCondylox

API名称

Podophyllotoxin

分子相关蛋白质

PDB Bank

1SA1

描述信息

DrugBank

DB01179

Drug Groups

approved

Description

Indication

For treatment of external genital warts (Condyloma acuminatum).

Pharmacology

Affected Organisms

Condyloma acuminatum

Absorption

Half Life

1.0 to 4.5 hours.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

DB08417

Drug information: experimental

Sigma Aldrich

P4405

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
100 mg in glass bottle
50 mg in poly bottle

858447

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
1 g in glass bottle
100 mg in glass bottle

81125

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
Other Notes
Inhibitor of microtubule assembly. Useful tool for tubulin studies1,2,3

TRC

P681000

Skin treatment for genital warts caused by some types of HPVs.

ChEBI

CHEBI:50305

参考文献

PubChem文献

数据源提供

• Gupta, R.S.; Cancer Research, 43, 505 (1983a)

• Kelly, M.G. & Hartwell, J.L.; J. of the Nat'l Cancer Inst., 14, 967 (1954)

• Gupta, R.S.; Somatic Cell Genetics, 7, 59 (1954)

• Duffield, A.M., J. Het. Chem., 1967, 4, 16, (ms)

• Nadkarni, M.V. et al., J.A.C.S., 1953, 75, 1308, (isol, derivs)

• Macdonald, D.I. et al., J.O.C., 1986, 51, 4749, (synth)

• Hartwell, J.L. et al., J.A.C.S., 1951, 73, 2909, (isol)

• Kamil, W.M. et al., Phytochemistry, 1986, 25, 2093, (biosynth)

• Jones, D.W. et al., Chem. Comm., 1987, 1797; 1989, 1370, (synth)

• Forsey, S.P. et al., J.O.C., 1989, 54, 4280, (synth)

• Wichers, H.J. et al., Phytochemistry, 1991, 30, 3601, (biosynth)

• Pelter, A. et al., Tetrahedron, 1994, 50, 10829, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1304A, (nmr)

• Stoll, A. et al., J.A.C.S., 1954, 76, 3103, (glucoside)

• Inamori, Y. et al., Chem. Pharm. Bull., 1986, 34, 3928, (props)

• Thurston, L.S. et al., J. Med. Chem., 1989, 32, 604, (pharmacol)

• Andersen, K.V. et al., J.C.S. Perkin 2, 1990, 1871, (cryst struct)

• Ayres, D.C. et al., Lignans, Chem. Biol. and Clinical Props., Cambridge, 1990, (rev)

• Sackett, D.L., Pharmacol. Ther., 1993, 59, 163, (rev)

• Andrews, R.C. et al., J.A.C.S., 1988, 110, 7854, (synth)

• Macdonald, D.I. et al., J.O.C., 1988, 43, 3663, (synth)

• Kaneko, T. et al., Tet. Lett., 1987, 28, 517, (synth)

• Ward, R.S., Synthesis, 1992, 719, (rev, synth, bibl)

• Jackson, D.E. et al., Phytochemistry, 1984, 23, 1029; 1037, (biosynth)

• Puri, H.S., Planta Med., 1988, 54, 269, (isol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 765

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 320A, (ir)

• Vyas, D.M. et al., Tet. Lett., 1986, 27, 3099, (synth)

• Van Speybroeck, R. et al., Tetrahedron, 1991, 47, 4675, (synth)

• Schrecker, A.W. et al., J.O.C., 1956, 21, 288; 381, (props, abs config)

• Gensler, W.J. et al., J.A.C.S., 1962, 84, 1748, (synth)

• Gensler, W.J. et al., J.O.C., 1966, 31, 3224, (synth)

• Ayres, D.C. et al., J.C.S. Perkin 1, 1972, 1343, (pmr)

• Petcher, T.J. et al., J.C.S. Perkin 2, 1973, 288, (cryst struct)

• Van der Eycken, J. et al., Tetrahedron, 1986, 42, 4297, (synth)

• Lim, Y.-H. et al., Arch. Pharmacal Res., 1999, 22, 208-212, (Angeloylpodophyllotoxin)

• Canel, C. et al., Phytochemistry, 2000, 54, 115-120, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EBB600

• Del Corral, J.M.M. et al., J. Nat. Prod., 1995, 58, 870, (synth, pmr, cmr)

• Zhao, C. et al., Chem. Pharm. Bull., 2001, 49, 773-775, (Isopodophyllotoxin 7-gentiobioside)

• Bush, E.J. et al., J.C.S. Perkin 1, 1996, 151, (synth)

• Berkowitz, D.B. et al., J.O.C., 2000, 65, 847-860, (synth, bibl)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

纯度

≥98%

95%

≥98.0% (HPLC)

Empirical Formula (Hill Notation)

C22H22O8

质检报告

下载链接

生物来源

Isol. from Podophyllum emodi, Diphylleia grayi and others

Cytostatic

药理学性质

生物活性机理

Reported to bind to tubulin

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

化合物信息

ID:1050