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

• ChemBase ID: 174766
• Molecular Formular: C21H30N5O14P
• Molecular Mass: 607.461761
• Monoisotopic Mass: 607.1526873
• SMILES: C(=C\C(=O)O)/C(=O)O.n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC)C
• Canonical SMILES: OC(=O)/C=C/C(=O)O.COC(=O)OCOP(=O)(CO[C@@H](Cn1cnc2c1ncnc2N)C)OCOC(=O)OC(C)C
• InChI: InChI=1S/C17H26N5O10P.C4H4O4/c1-11(2)32-17(24)28-9-31-33(25,30-8-27-16(23)26-4)10-29-12(3)5-22-7-21-13-14(18)19-6-20-15(13)22;5-3(6)1-2-4(7)8/h6-7,11-12H,5,8-10H2,1-4H3,(H2,18,19,20);1-2H,(H,5,6)(H,7,8)/b;2-1+/t12-,33?;/m1./s1
• InChIKey: YUQOAWMYXXJXNV-OXCDREKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid [(methoxycarbonyl)oxy]methyl {[(propan-2-yloxy)carbonyl]oxy}methyl {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
• IUPAC Traditional name: fumaric acid [(isopropoxycarbonyl)oxy]methyl [(methoxycarbonyl)oxy]methyl {[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methanephosphonate
• Synonyms: 5-[[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-2,4,6,8-tetraoxa-5-phosphanonanedioic Acid (1-Methylethyl,methyl) Ester 5-Oxide Fumarate; MOC-POC PMPA Fumarate; MOC-POC Tenofovir Fumarate Salt(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164230676
• PubChem CID: 71750817

CALCULATED PROPERTIES

• Acid pKa: 18.587572
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 1.7416656
• LogD (pH = 7.4): 1.8904954
• Log P: 1.8927723
• Molar Refractivity: 109.4208 cm^3
• Polarizability: 44.066406 Å^3
• Polar Surface Area: 185.44 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 105-107°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M566990

Tenofovir (T018500) impurity.