(2S)-2-(1,3-dioxo-2,3,5,6-tetrahydro-1H-isoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid

• ChemBase ID: 153953
• Molecular Formular: C19H16N2O4
• Molecular Mass: 336.34134
• Monoisotopic Mass: 336.111007
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)O)N1C(=O)C2=CCCC=C2C1=O
• Canonical SMILES: OC(=O)[C@@H](N1C(=O)C2=CCCC=C2C1=O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C19H16N2O4/c22-17-13-6-1-2-7-14(13)18(23)21(17)16(19(24)25)9-11-10-20-15-8-4-3-5-12(11)15/h3-8,10,16,20H,1-2,9H2,(H,24,25)/t16-/m0/s1
• InChIKey: LMAZUAXDZRILNJ-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(1,3-dioxo-2,3,5,6-tetrahydro-1H-isoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-(1,3-dioxo-5,6-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid
• Synonyms: N-Phthalyl-L-tryptophan; RG108

Database IDs

• CAS Number: 48208-26-0
• PubChem SID: 162248092; 24724594
• PubChem CID: 16079004

CALCULATED PROPERTIES

• Acid pKa: 3.9100463
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.6481865
• LogD (pH = 7.4): -0.96417207
• Log P: 2.2441998
• Molar Refractivity: 91.7627 cm^3
• Polarizability: 35.63759 Å^3
• Polar Surface Area: 90.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H14N2O4

DETAILS

Sigma Aldrich - R8279

Biochem/physiol Actions
RG108 is a DNA methyltransferase (DMNT) inhibitor. It reactivates tumor suppressor gene expression (p16, SFRP1, secreted frizzled related protein-1, and TIMP-3) in tumor cells by DNA demethylation. RG108 also inhibits human tumor cell line (HCT116, NALM-6) proliferation and increased doubling time in culture.