(10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one

• ChemBase ID: 120128
• Molecular Formular: C21H20O8
• Molecular Mass: 400.3787
• Monoisotopic Mass: 400.1158176
• SMILES: [C@H]12[C@@H]([C@@H](c3c([C@@H]1O)cc1c(c3)OCO1)c1cc(c(c(c1)OC)O)OC)C(=O)OC2
• Canonical SMILES: COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
• InChI: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19-/m0/s1
• InChIKey: YVCVYCSAAZQOJI-BTINSWFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one; (10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1,3(7),8-trien-12-one
• IUPAC Traditional name: (10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one; (10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1,3(7),8-trien-12-one
• Synonyms: (5R,5aR,8aR,9R)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; 4'-Demethylepipodophyllotoxin

Database IDs

• CAS Number: 6559-91-7
• PubChem SID: 162214481
• PubChem CID: 122667

CALCULATED PROPERTIES

• Acid pKa: 9.330433
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.4768405
• LogD (pH = 7.4): 1.4718733
• Log P: 1.4769042
• Molar Refractivity: 99.4227 cm^3
• Polarizability: 39.10291 Å^3
• Polar Surface Area: 103.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: DNA topoisomerase II inhibitor

Product Information

• Biological Source: Isol. from Polygala paenea
• Application(s): Antimitotic agent