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518-28-5 molecular structure
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(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

ChemBase ID: 1050
Molecular Formular: C22H22O8
Molecular Mass: 414.40528
Monoisotopic Mass: 414.13146766
SMILES and InChIs

SMILES:
O1C[C@H]2[C@@H]([C@@H](c3c([C@@H]2O)cc2OCOc2c3)c2cc(OC)c(OC)c(OC)c2)C1=O
Canonical SMILES:
COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
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

Cite this record

CBID:1050 http://www.chembase.cn/molecule-1050.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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(9),2,7-trien-12-one
IUPAC Traditional name
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
condylox
Brand Name
Podophyllotoxin 7
Podophyllotoxin
Synonyms
Podophyllinic acid lactone
Podofilox
(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)-one
(-)-Podophyllotoxin
Condyline
Condylox
NSC 24818
Podofilox
Podophyllotoxin
Warticon
Podofilox
(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
Podophyllotoxin
(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
9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONE
CAS Number
518-28-5
477-47-4
EC Number
208-250-4
MDL Number
MFCD00075290
Beilstein Number
99163
PubChem SID
24887649
24277731
160964513
46505716
24888464
PubChem CID
10607

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.015751  H Acceptors
H Donor LogD (pH = 5.5) 1.6227983 
LogD (pH = 7.4) 1.6227982  Log P 1.6227983 
Molar Refractivity 103.905 cm3 Polarizability 41.000076 Å3
Polar Surface Area 92.68 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.37  LOG S -3.56 
Solubility (Water) 1.14e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
100 mg/L expand Show data source
120mg/L in Water expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
Ethanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
154-158°C expand Show data source
182 - 184°C expand Show data source
183-184 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -110.7°, c = 1 in chloroform expand Show data source
[α]20/D -132±4°, c = 1% in chloroform expand Show data source
Hydrophobicity(logP)
1.444 expand Show data source
1.5 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
Storage Warning
Very Hygroscopic expand Show data source
RTECS
LV2500000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
3462 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
21-25-36/37/38 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H310-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P280-P302 + P350-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3462 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Mechanism of Action
Cell division inhibitor expand Show data source
Inhibitor of human DNA topoisomerase II expand Show data source
Reported to bind to tubulin expand Show data source
Purity
≥98% expand Show data source
≥98.0% (HPLC) expand Show data source
95% expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
Isol. from Podophyllum emodi, Diphylleia grayi and others expand Show data source
Application(s)
Cytostatic expand Show data source
Empirical Formula (Hill Notation)
C22H22O8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB01179 external link
Item Information
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
DrugBank - DB08417 external link
Drug information: experimental
Sigma Aldrich - P4405 external link
Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
100 mg in glass bottle
50 mg in poly bottle
Sigma Aldrich - 858447 external link
Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
Packaging
1 g in glass bottle
100 mg in glass bottle
Sigma Aldrich - 81125 external link
Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
Other Notes
Inhibitor of microtubule assembly. Useful tool for tubulin studies1,2,3
Toronto Research Chemicals - P681000 external link
Skin treatment for genital warts caused by some types of HPVs.

REFERENCES

REFERENCES

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