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

Beilstein号

MDL号

CAS号

EC号

PubChem SID

2427773116096451324887649248884644650571650139208

PubChem CID

10607

DrugBank ID

DB01179

专利号

WO2007129062US2007196325US2007203104WO2007114549US2005137207WO2007089864EP1872775US2006079563US2007202055US2007244076US2006106065WO2005112919US2005267175WO2005056549

UniProt数据库

Q9CQF6Q8MJ44Q20390O35448P71043P41539Q5VQL3P27401P07694Q6DJH2Q60676Q9VKH6O93209Q8HXW6P25321

PubMed文献链接

226217722379888381128252316154415803102

MetaboLights数据库

MTBLS2384MTBLS2145

HMDB数据库

HMDB0031452

BRENDA数据库

5.6.2.23.2.1.21

CHEBI ID

CHEBI:45070CHEBI:50305CHEBI:8280

CompTox数据库

DTXSID3045645

维基百科标题

Podophyllotoxin

Drug Central Database

KNApSAcK数据库

SureChEMBL数据库

BRENDA Ligand数据库

KEGG DRUG Database

CHEMBL

BKMS React数据库

PDBeChem数据库

Reaxys Registry

PDB数据库

ACToR数据库

KEGG ID

LINCS数据库

数据登录号

化合物性质

安全信息

H301-H310-H315-H319-H335

2-8°C

急性毒性（口服，皮肤接触，吸入），类别1,2,3

药理学性质

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

Reported to bind to tubulin

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.; Somatic Cell Genetics, 7, 59 (1954)

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

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

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

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

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

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

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

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

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

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

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

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

参考文献

PubChem文献

数据源提供

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

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

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

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

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

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

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

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

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

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

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

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

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

生物活性

PubChem BioAssay

数据登录号

Beilstein号

MDL号

CAS号

EC号

PubChem SID

2427773116096451324887649248884644650571650139208

PubChem CID

10607

DrugBank ID

DB01179

专利号

WO2007129062US2007196325US2007203104WO2007114549US2005137207WO2007089864EP1872775US2006079563US2007202055US2007244076US2006106065WO2005112919US2005267175WO2005056549

UniProt数据库

Q9CQF6Q8MJ44Q20390O35448P71043P41539Q5VQL3P27401P07694Q6DJH2Q60676Q9VKH6O93209Q8HXW6P25321

PubMed文献链接

226217722379888381128252316154415803102

MetaboLights数据库

MTBLS2384MTBLS2145

HMDB数据库

HMDB0031452

BRENDA数据库

5.6.2.23.2.1.21

CHEBI ID

CHEBI:45070CHEBI:50305CHEBI:8280

CompTox数据库

DTXSID3045645

维基百科标题

Podophyllotoxin

Drug Central Database

KNApSAcK数据库

SureChEMBL数据库

BRENDA Ligand数据库

KEGG DRUG Database

CHEMBL

BKMS React数据库

PDBeChem数据库

Reaxys Registry

PDB数据库

ACToR数据库

KEGG ID

LINCS数据库

化合物性质

安全信息

H301-H310-H315-H319-H335

2-8°C

急性毒性（口服，皮肤接触，吸入），类别1,2,3

药理学性质

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

Reported to bind to tubulin

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

化合物信息

ID:1050