4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-{2-[hydroxy(13C)methyl](2,3,4,5-13C4,1-15N)pyrrolidin-1-yl}-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

• ChemBase ID: 160897
• Molecular Formular: C23H26ClN7O3
• Molecular Mass: 489.90732309
• Monoisotopic Mass: 489.19237449
• SMILES: c1c(c(cc(c1)CNc1nc(ncc1C(=O)NCc1ncccn1)[15N]1[13CH2][13CH2][13CH2][13CH]1[13CH2]O)Cl)OC
• Canonical SMILES: O[13CH2][13CH]1[13CH2][13CH2][13CH2][15N]1c1ncc(c(n1)NCc1ccc(c(c1)Cl)OC)C(=O)NCc1ncccn1
• InChI: InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/i2+1,4+1,9+1,14+1,16+1,31+1
• InChIKey: WEAJZXNPAWBCOA-PVAAWCPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-{2-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄,1-^1^5N)pyrrolidin-1-yl}-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
• IUPAC Traditional name: 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-{2-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄,1-^1^5N)pyrrolidin-1-yl}-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
• Synonyms: (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine-13C5,15N; 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide-13C5,15N; TA 1790-13C5,15N; Avanafil-13C5,15N

Database IDs

• PubChem SID: 162255032
• PubChem CID: 71313531

CALCULATED PROPERTIES

• Acid pKa: 13.712366
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 2.4773307
• LogD (pH = 7.4): 2.7731328
• Log P: 2.778813
• Molar Refractivity: 131.751 cm^3
• Polarizability: 48.31286 Å^3
• Polar Surface Area: 125.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A794672

A labelled phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.

REFERENCES

• Hatzimouratidis, K., et al.: Drugs, 68, 231 (2008)