(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: 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

NAMES AND DATABASE IDS

Names

• 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[7.7.0.0^3,^7.0^1^1,^1^5]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,^7.0^1^1,^1^5]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[7.7.0.0^3,^7.0^1^1,^1^5]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

Database IDs

• CAS Number: 518-28-5; 477-47-4
• EC Number: 208-250-4
• MDL Number: MFCD00075290
• Beilstein Number: 99163
• PubChem SID: 24277731; 24887649; 160964513; 46505716; 24888464
• PubChem CID: 10607

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.015751
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.6227983
• LogD (pH = 7.4): 1.6227982
• Log P: 1.6227983
• Molar Refractivity: 103.905 cm^3
• Polarizability: 41.000076 Å^3
• Polar Surface Area: 92.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.37
• LOG S: -3.56
• Solubility (Water): 1.14e-01 g/l

PROPERTIES

Physical Property

• Solubility: 100 mg/L; 120mg/L in Water; Acetone; Chloroform; Ethanol
• Apperance: White to Off-White Solid
• Melting Point: 154-158°C; 182 - 184°C; 183-184 °C(lit.)
• Optical Rotation: [α]20/D -110.7°, c = 1 in chloroform; [α]20/D -132±4°, c = 1% in chloroform
• Hydrophobicity(logP): 1.444; 1.5

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Very Hygroscopic
• RTECS: LV2500000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 21-25-36/37/38
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H315-H319-H335
• GHS Precautionary statements: P261-P280-P302 + P350-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Cell division inhibitor; Inhibitor of human DNA topoisomerase II; Reported to bind to tubulin

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); 95%
• Biological Source: Isol. from Podophyllum emodi, Diphylleia grayi and others
• Application(s): Cytostatic
• Empirical Formula (Hill Notation): C22H22O8

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

DrugBank - 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

Sigma Aldrich - 858447

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

Sigma Aldrich - 81125

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

Toronto Research Chemicals - P681000

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

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