N-(4-{[3-butyl-2,6-dioxo-1-(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]methyl}phenyl)acetamide

• ChemBase ID: 2962
• Molecular Formular: C21H25N5O3
• Molecular Mass: 395.4549
• Monoisotopic Mass: 395.19573969
• SMILES: O=c1n(CC=C)c(=O)c2c(n1CCCC)nc([nH]2)Cc1ccc(cc1)NC(=O)C
• Canonical SMILES: CCCCn1c2nc([nH]c2c(=O)n(c1=O)CC=C)Cc1ccc(cc1)NC(=O)C
• InChI: InChI=1S/C21H25N5O3/c1-4-6-12-25-19-18(20(28)26(11-5-2)21(25)29)23-17(24-19)13-15-7-9-16(10-8-15)22-14(3)27/h5,7-10H,2,4,6,11-13H2,1,3H3,(H,22,27)(H,23,24)
• InChIKey: XFOWZKUTPKXWIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-{[3-butyl-2,6-dioxo-1-(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]methyl}phenyl)acetamide
• IUPAC Traditional name: N-(4-{[3-butyl-2,6-dioxo-1-(prop-2-en-1-yl)-7H-purin-8-yl]methyl}phenyl)acetamide
• Synonyms: 1-Allyl-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine; trans-2-(3-Bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylic Acid 2-Propenyl Ester; Bromoridane N-Carboxylic Acid Allyl Ester; Alloc Bromoridane

Database IDs

• CAS Number: 117348-70-6
• PubChem SID: 160966409; 46504813
• PubChem CID: 447076

CALCULATED PROPERTIES

JChem

• Lipinski's Rule of Five: true
• Acid pKa: 7.8589892
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4792786
• LogD (pH = 7.4): 2.369511
• Log P: 2.480942
• Molar Refractivity: 111.9964 cm^3
• Polarizability: 41.20556 Å^3
• Polar Surface Area: 98.4 Å^2
• Rotatable Bonds: 8

ALOGPS 2.1

• Solubility (Water): 1.60e-01 g/l
• Log P: 2.69
• LOG S: -3.39

DETAILS

DrugBank - DB03267

Drug information: experimental

Toronto Research Chemicals - A549675

Alloc Bromoridane is used as an anticoccidial agent. Alloc Bromoridane is an intermediate of Febrifugine and Halofuginone (H102500), as inhibitors of prolyl-tRNA synthetase.