5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 670
• Molecular Formular: C8H11Cl2N3O2
• Molecular Mass: 252.09784
• Monoisotopic Mass: 251.02283197
• SMILES: ClCCN(CCCl)c1c(=O)[nH]c(=O)[nH]c1
• Canonical SMILES: ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
• InChI: InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
• InChIKey: IDPUKCWIGUEADI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: uracil mustard
• Brand Name: Aminouracil Mustard; Chlorethaminacil; Demethyldopan; Desmethyldopan; Haemanthamine; Nordopan; Uracil nitrogen mustard; Uracillost; Uracilmostaza; Uramustin; Uramustine
• Synonyms: Uracil mustard

Database IDs

• CAS Number: 66-75-1
• PubChem SID: 46506168; 160964133
• PubChem CID: 6194

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.048361
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.40513447
• LogD (pH = 7.4): 0.3957709
• Log P: 0.40531176
• Molar Refractivity: 58.3501 cm^3
• Polarizability: 21.927856 Å^3
• Polar Surface Area: 61.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.79
• LOG S: -2.28
• Solubility (Water): 1.32e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1070 mg/L
• Hydrophobicity(logP): 1.2

DETAILS

DrugBank - DB00791

• Drug Groups: approved
• Description: Nitrogen mustard derivative of uracil. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage. [PubChem]
• Indication: Used for its antineoplastic properties.
• Pharmacology: Uracil Mustard selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Uracil Mustard-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.
• Affected Organisms: Humans and other mammals
• Protein Binding: 5%
• External Links: Wikipedia