8-[(benzylsulfanyl)methyl]-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 154392
• Molecular Formular: C15H16N4O2S
• Molecular Mass: 316.37814
• Monoisotopic Mass: 316.09939677
• SMILES: Cn1c2c(c(=O)n(c1=O)C)[nH]c(n2)CSCc1ccccc1
• Canonical SMILES: Cn1c2nc([nH]c2c(=O)n(c1=O)C)CSCc1ccccc1
• InChI: InChI=1S/C15H16N4O2S/c1-18-13-12(14(20)19(2)15(18)21)16-11(17-13)9-22-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3,(H,16,17)
• InChIKey: FEHAMBYTUPDFJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(benzylsulfanyl)methyl]-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-[(benzylsulfanyl)methyl]-1,3-dimethyl-7H-purine-2,6-dione
• Synonyms: 8-Benzylsulfanylmethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione; 8-[(Benzylthio)methyl]theophylline; Theophylline, 8-[(benzylthio)methyl]; TPBM

Database IDs

• CAS Number: 6466-43-9
• MDL Number: MFCD11114397
• PubChem SID: 162248531
• PubChem CID: 262425

CALCULATED PROPERTIES

• Acid pKa: 7.1661725
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5798914
• LogD (pH = 7.4): 1.2372806
• Log P: 1.5880128
• Molar Refractivity: 86.5172 cm^3
• Polarizability: 32.344296 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H16N4O2S

DETAILS

Sigma Aldrich - T5202

Biochem/physiol Actions
TPBM is a potent inhibitor of estrogen receptor α via blocking ERα binding to consensus estrogen response element (cERE) DNA. Estrogen receptor α (ERα) plays an important role in several human cancers. Current ERα antagonists bind in the receptor ligand binding pocket and compete for binding with estrogenic ligands. TPBM instead inhibits ERα via binding to consensus estrogen response element (cERE) DNA. TPBM is not toxic to cells and does not effect estrogen-independent cell growth. TPBM does not act by chelating the zinc in ERs zinc fingers and differs from known ERα inhibitors.