(2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-hydroxypropanoic acid

• ChemBase ID: 161255
• Molecular Formular: C18H13NO7
• Molecular Mass: 355.29832
• Monoisotopic Mass: 355.06920176
• SMILES: c12c(ccc(c1)[C@H]([C@H](N1C(=O)c3c(C1=O)cccc3)C(=O)O)O)OCO2
• Canonical SMILES: OC(=O)[C@@H](N1C(=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+/m0/s1
• InChIKey: ZMFOCUAXRJOPCJ-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-hydroxypropanoic acid
• IUPAC Traditional name: (2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-(1,3-dioxoisoindol-2-yl)-3-hydroxypropanoic acid
• Synonyms: (R,S)-rel-α-(1,3-Benzodioxol-5-ylhydroxymethyl)-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic Acid; 1,3-Benzodioxole-N-phthalimido DL-threo-Droxidopa

Database IDs

• PubChem SID: 162255390
• PubChem CID: 11024665

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; Methanol
• Apperance: Light Yellow Solid

DETAILS

Toronto Research Chemicals - B203500

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