(2S,3S,6R)-6-[(4S)-4-amino-4-hydroxy-2-oxo-1,2,3,4-tetrahydropyrimidin-1-yl]-3-[(3S)-3-amino-5-(1-methylcarbamimidamido)pentanamido]-3,6-dihydro-2H-pyran-2-carboxylic acid

• ChemBase ID: 4209
• Molecular Formular: C17H28N8O6
• Molecular Mass: 440.45422
• Monoisotopic Mass: 440.21318066
• SMILES: N=C(N)N(C)CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(=O)O)N1C=C[C@@](N)(O)NC1=O
• Canonical SMILES: N[C@H](CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(=O)O)N1C=C[C@@](NC1=O)(N)O)CCN(C(=N)N)C
• InChI: InChI=1S/C17H28N8O6/c1-24(15(19)20)6-4-9(18)8-11(26)22-10-2-3-12(31-13(10)14(27)28)25-7-5-17(21,30)23-16(25)29/h2-3,5,7,9-10,12-13,30H,4,6,8,18,21H2,1H3,(H3,19,20)(H,22,26)(H,23,29)(H,27,28)/t9-,10-,12+,13-,17-/m0/s1
• InChIKey: MVFPGTZTOAHVBP-HXYLPHSESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,6R)-6-[(4S)-4-amino-4-hydroxy-2-oxo-1,2,3,4-tetrahydropyrimidin-1-yl]-3-[(3S)-3-amino-5-(1-methylcarbamimidamido)pentanamido]-3,6-dihydro-2H-pyran-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,6R)-6-[(4S)-4-amino-4-hydroxy-2-oxo-3H-pyrimidin-1-yl]-3-[(3S)-3-amino-5-(1-methylcarbamimidamido)pentanamido]-3,6-dihydro-2H-pyran-2-carboxylic acid
• Synonyms: TETRAHEDRAL INTERMEDIATE OF BLASTICIDIN S

Database IDs

• PubChem SID: 160967641; 46508650
• PubChem CID: 5287847

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3330476
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -9.092921
• LogD (pH = 7.4): -6.3752227
• Log P: -5.263466
• Molar Refractivity: 119.3272 cm^3
• Polarizability: 41.76962 Å^3
• Polar Surface Area: 233.35 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.19
• LOG S: -2.83
• Solubility (Water): 6.59e-01 g/l

DETAILS

DrugBank - DB04649

Drug information: experimental