(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

• ChemBase ID: 72971
• Molecular Formular: C22H22O8
• Molecular Mass: 414.40528
• Monoisotopic Mass: 414.13146766
• SMILES: c12c(cc3c(c1)[C@@H]([C@@H]1[C@@H](C3c3cc(c(c(c3)OC)OC)OC)C(=O)OC1)O)OCO2
• Canonical SMILES: COc1cc(cc(c1OC)OC)C1[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-LBXUKJEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: (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
• Synonyms: Podofilox; Condylox; Podophyllotoxin

Database IDs

• CAS Number: 518-28-5
• PubChem SID: 162037891
• PubChem CID: 12309632

CALCULATED PROPERTIES

• 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

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2345

Research Area: Cancer
Biological Activity:
Podophyllotoxin(Podofilox) is 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. [1]

REFERENCES

• http://www.drugbank.ca/drugs/DB01179