(2E)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide

• ChemBase ID: 3835
• Molecular Formular: C13H19N3O5S2
• Molecular Mass: 361.43706
• Monoisotopic Mass: 361.07661272
• SMILES: CSC[S@](=O)C[C@H](CO)NC(=O)/C=C/c1c(C)[nH]c(=O)[nH]c1=O
• Canonical SMILES: CSC[S@](=O)C[C@@H](NC(=O)/C=C/c1c(C)[nH]c(=O)[nH]c1=O)CO
• InChI: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1
• InChIKey: XKLZIVIOZDNKEQ-CLQLPEFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide
• IUPAC Traditional name: (2E)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl]-3-(4-methyl-2,6-dioxo-1,3-dihydropyrimidin-5-yl)prop-2-enamide
• Synonyms: Sparsomycin

Database IDs

• PubChem SID: 160967272; 46505251
• PubChem CID: 9543443

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.925983
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.4822292
• LogD (pH = 7.4): -2.4834285
• Log P: -2.4821508
• Molar Refractivity: 91.6654 cm^3
• Polarizability: 34.5365 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.32
• LOG S: -2.36
• Solubility (Water): 1.59e+00 g/l

DETAILS

DrugBank - DB04222

• Drug Groups: experimental
• Description: An antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems. [PubChem]