(2E)-but-2-enedioic acid; bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate

• ChemBase ID: 866338
• Molecular Formular: C23H34N5O14P
• Molecular Mass: 635.514921
• Monoisotopic Mass: 635.18398742
• SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.OC(=O)/C=C/C(=O)O
• Canonical SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
• InChIKey: VCMJCVGFSROFHV-WZGZYPNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
• IUPAC Traditional name: fumaric acid; pmpa prodrug
• Synonyms: Tenofovir dipivoxil FuMarate(TDF); 泰诺福韦酯富马酸盐

Database IDs

• CAS Number: 202138-50-9

CALCULATED PROPERTIES

• Acid pKa: 18.587572
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 2.5019405
• LogD (pH = 7.4): 2.650774
• Log P: 2.653051
• Molar Refractivity: 118.5882 cm^3
• Polarizability: 47.692413 Å^3
• Polar Surface Area: 185.44 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false