CAS 518-28-5|CAS 477-47-4|(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadec...

General Information

Structure

Molecular Formula

C₂₂H₂₂O₈

Molecular Mass

414.40528

Exact Mass

414.13146766

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

1.62

LogD (pH = 5.5)

1.62

Log P

1.62

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.40

Polar Surface Area

92.68

Polarizability

41.81

Molar Refractivity

103.90

LOG S

-3.62

Data Source

Names and Identifiers

Synonyms

(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 Traditional name

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 name

(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

Brand Name

Podophyllotoxin 7PodophyllotoxinCondylox

API Name

Podophyllotoxin

Names and Identifiers

Registration numbers

Beilstein Number

MDL Number

CAS Number

EC Number

PubChem SID

2427773116096451324887649248884644650571650139208

PubChem CID

10607

DrugBank ID

DB01179

Patent number

WO2007129062US2007196325US2007203104WO2007114549US2005137207WO2007089864EP1872775US2006079563US2007202055US2007244076US2006106065WO2005112919US2005267175WO2005056549

UniProt Database

Q9CQF6Q8MJ44Q20390O35448P71043P41539Q5VQL3P27401P07694Q6DJH2Q60676Q9VKH6O93209Q8HXW6P25321

PubMed Citation Links

226217722379888381128252316154415803102

MetaboLights Database

MTBLS2384MTBLS2145

HMDB Database

HMDB0031452

BRENDA Database

5.6.2.23.2.1.21

CHEBI ID

CHEBI:45070CHEBI:50305CHEBI:8280

CompTox Database

DTXSID3045645

Wikipedia Title

Podophyllotoxin

Drug Central Database

3,481

KNApSAcK Database

C00000610

SureChEMBL Database

SCHEMBL42243

BRENDA Ligand Database

KEGG DRUG Database

CHEMBL

BKMS React Database

PDBeChem Database

Reaxys Registry

Protein Data Bank

ACToR Database

KEGG ID

LINCS Database

Registration numbers

Properties

Safety Information

H301-H310-H315-H319-H335

2-8°C

Acute toxicity (oral, dermal, inhalation), categories 1,2,3

Pharmacology Properties

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

Reported to bind to tubulin

Properties

Related Proteins

PDB Bank

1SA1

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

IUPAC name

Brand Name

Podophyllotoxin 7PodophyllotoxinCondylox

API Name

Podophyllotoxin

Related Proteins

PDB Bank

1SA1

Bioactivity

PubChem BioAssay

Registration numbers

Beilstein Number

MDL Number

CAS Number

EC Number

PubChem SID

2427773116096451324887649248884644650571650139208

PubChem CID

10607

DrugBank ID

DB01179

Patent number

WO2007129062US2007196325US2007203104WO2007114549US2005137207WO2007089864EP1872775US2006079563US2007202055US2007244076US2006106065WO2005112919US2005267175WO2005056549

UniProt Database

Q9CQF6Q8MJ44Q20390O35448P71043P41539Q5VQL3P27401P07694Q6DJH2Q60676Q9VKH6O93209Q8HXW6P25321

PubMed Citation Links

226217722379888381128252316154415803102

MetaboLights Database

MTBLS2384MTBLS2145

HMDB Database

HMDB0031452

BRENDA Database

5.6.2.23.2.1.21

CHEBI ID

CHEBI:45070CHEBI:50305CHEBI:8280

CompTox Database

DTXSID3045645

Wikipedia Title

Podophyllotoxin

Drug Central Database

3,481

KNApSAcK Database

C00000610

SureChEMBL Database

SCHEMBL42243

BRENDA Ligand Database

KEGG DRUG Database

CHEMBL

BKMS React Database

PDBeChem Database

Reaxys Registry

Protein Data Bank

ACToR Database

KEGG ID

LINCS Database

Properties

Safety Information

H301-H310-H315-H319-H335

2-8°C

Acute toxicity (oral, dermal, inhalation), categories 1,2,3

Pharmacology Properties

Inhibitor of human DNA topoisomerase II

Cell division inhibitor

Reported to bind to tubulin

Molecule Details

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]

References

PubChem Literature

From Data Sources

• 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)

Molecule

ID:1050