3-(3-hydroxypropyl)-8-[2-(3-methoxyphenyl)ethenyl]-7-methyl-1-(prop-2-yn-1-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 153247
• Molecular Formular: C21H22N4O4
• Molecular Mass: 394.42378
• Monoisotopic Mass: 394.1641052
• SMILES: Cn1c(nc2c1c(=O)n(c(=O)n2CCCO)CC#C)/C=C/c1cccc(c1)OC
• Canonical SMILES: OCCCn1c(=O)n(CC#C)c(=O)c2c1nc(n2C)/C=C/c1cccc(c1)OC
• InChI: InChI=1S/C21H22N4O4/c1-4-11-25-20(27)18-19(24(21(25)28)12-6-13-26)22-17(23(18)2)10-9-15-7-5-8-16(14-15)29-3/h1,5,7-10,14,26H,6,11-13H2,2-3H3
• InChIKey: FWLDDFYHEQMIGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-hydroxypropyl)-8-[2-(3-methoxyphenyl)ethenyl]-7-methyl-1-(prop-2-yn-1-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 3-(3-hydroxypropyl)-8-[2-(3-methoxyphenyl)ethenyl]-7-methyl-1-(prop-2-yn-1-yl)purine-2,6-dione
• Synonyms: 3-(3-Hydroxypropyl)-8-(m-methoxystyryl)-7-methyl-1-propargylxanthine; MSX-2

Database IDs

• CAS Number: 261717-18-4
• MDL Number: MFCD11046007
• PubChem SID: 162247386
• PubChem CID: 10046145

CALCULATED PROPERTIES

• Acid pKa: 15.931649
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.4598205
• LogD (pH = 7.4): 1.4598206
• Log P: 1.4598206
• Molar Refractivity: 109.8892 cm^3
• Polarizability: 40.368633 Å^3
• Polar Surface Area: 87.9 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~14 mg/mL; H2O: insoluble
• Apperance: pale yellow solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H22N4O4

DETAILS

Sigma Aldrich - M3443

Biochem/physiol Actions
Selective A2A adenosine receptor antagonist