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

• ChemBase ID: 178150
• Molecular Formular: C23H34N5O14P
• Molecular Mass: 635.514921
• Monoisotopic Mass: 635.18398742
• SMILES: n1cnc2c(c1N)ncn2C[C@@H](OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C.C(=C\C(=O)O)/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-;/m0./s1
• InChIKey: VCMJCVGFSROFHV-KZHAMYRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2S)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
• IUPAC Traditional name: fumaric acid bis[(isopropoxycarbonyl)oxy]methyl {[(2S)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methanephosphonate
• Synonyms: 5-[[(1S)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-2,4,6,8-tetraoxa-5-phosphanonanedioic Acid 1,9-Bis(1-methylethyl) Ester 5-Oxide (2E)-2-Butenedioate; (S)-Tenofovir Disoproxil Fumarate

Database IDs

• PubChem SID: 164234060
• PubChem CID: 5282462

CALCULATED PROPERTIES

• Acid pKa: 18.587572
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 2.5019443
• 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

DETAILS

Toronto Research Chemicals - T018506

The S-enatiomeric impurity of the antiviral Tenofovir Disoproxil Fumarate (T018505).