4-[3,7-dimethyl-2,6-dioxo-1-(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]benzene-1-sulfonic acid

• ChemBase ID: 133041
• Molecular Formular: C16H16N4O5S
• Molecular Mass: 376.38704
• Monoisotopic Mass: 376.08414063
• SMILES: Cn1c2c(nc1c1ccc(cc1)S(=O)(=O)O)n(c(=O)n(c2=O)CC=C)C
• Canonical SMILES: C=CCn1c(=O)n(C)c2c(c1=O)n(C)c(n2)c1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C16H16N4O5S/c1-4-9-20-15(21)12-14(19(3)16(20)22)17-13(18(12)2)10-5-7-11(8-6-10)26(23,24)25/h4-8H,1,9H2,2-3H3,(H,23,24,25)
• InChIKey: CDMZOKMMANFJMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[3,7-dimethyl-2,6-dioxo-1-(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]benzene-1-sulfonic acid
• IUPAC Traditional name: 4-[3,7-dimethyl-2,6-dioxo-1-(prop-2-en-1-yl)purin-8-yl]benzenesulfonic acid
• Synonyms: 1-Allyl-3,7-dimethyl-8-sulfophenylxanthine

Database IDs

• CAS Number: 149981-25-9
• MDL Number: MFCD00083167
• PubChem SID: 162227318; 24277693
• PubChem CID: 1365

CALCULATED PROPERTIES

• Acid pKa: -2.3726575
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.98511547
• LogD (pH = 7.4): -0.98511755
• Log P: -0.58539104
• Molar Refractivity: 104.718 cm^3
• Polarizability: 36.141582 Å^3
• Polar Surface Area: 112.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white solid
• Absorption Wavelength: εmax/203 nm, methanol 28,200; εmax/239 nm, methanol 21,900; εmax/301 nm, methanol 18,200

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA2A(135), ADORA2B(136)rat ... Adora1(29290), Adora2a(25369)

DETAILS

Sigma Aldrich - A145

Biochem/physiol Actions
Weak A2 adenosine receptor antagonist.