(2R,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-[1,3-dioxo-2,3-dihydro(2-15N)-1H-isoindol-2-yl]-3-hydroxy(1,2-13C2)propanoic acid

• ChemBase ID: 161256
• Molecular Formular: C18H13NO7
• Molecular Mass: 358.27703857
• Monoisotopic Mass: 358.07294633
• SMILES: c12c(ccc(c1)[C@H]([13C@@H]([15N]1C(=O)c3c(C1=O)cccc3)[13C](=O)O)O)OCO2
• Canonical SMILES: O[13C](=O)[13C@H]([15N]1C(=O)c2c(C1=O)cccc2)[C@@H](c1ccc2c(c1)OCO2)O
• InChI: InChI=1S/C18H13NO7/c20-15(9-5-6-12-13(7-9)26-8-25-12)14(18(23)24)19-16(21)10-3-1-2-4-11(10)17(19)22/h1-7,14-15,20H,8H2,(H,23,24)/t14-,15-/m1/s1/i14+1,18+1,19+1
• InChIKey: ZMFOCUAXRJOPCJ-YDIIICFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-[1,3-dioxo-2,3-dihydro(2-^1^5N)-1H-isoindol-2-yl]-3-hydroxy(1,2-^1^3C₂)propanoic acid
• IUPAC Traditional name: (2R,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-[1,3-dioxo(2-^1^5N)isoindol-2-yl]-3-hydroxy(1,2-^1^3C₂)propanoic acid
• Synonyms: (R,S)-rel-α-(1,3-Benzodioxol-5-ylhydroxymethyl)-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic Acid-13C2,15N; 1,3-Benzodioxole-N-phthalimido DL-threo-Droxidopa-13C2,15N

Database IDs

• PubChem SID: 162255391
• PubChem CID: 71313696

CALCULATED PROPERTIES

• Acid pKa: 2.8559692
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.2674536
• LogD (pH = 7.4): -2.1649678
• Log P: 1.3244103
• Molar Refractivity: 86.3834 cm^3
• Polarizability: 33.007805 Å^3
• Polar Surface Area: 113.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B203502

Intermediate in the preparation of labelled DL-threo-Droxidopa, an antiparkinsonian.