(2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[methyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

• ChemBase ID: 3175
• Molecular Formular: C14H23N5O5
• Molecular Mass: 341.36292
• Monoisotopic Mass: 341.16991886
• SMILES: CCCN(C)C(=O)[C@@H]1OC(=C[C@H](NC(=N)N)[C@H]1NC(=O)C)C(=O)O
• Canonical SMILES: CCCN(C(=O)[C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)NC(=N)N)C(=O)O)C
• InChI: InChI=1S/C14H23N5O5/c1-4-5-19(3)12(21)11-10(17-7(2)20)8(18-14(15)16)6-9(24-11)13(22)23/h6,8,10-11H,4-5H2,1-3H3,(H,17,20)(H,22,23)(H4,15,16,18)/t8-,10+,11+/m0/s1
• InChIKey: QPJWMZVTNXFTKV-JMJZKYOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[methyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4-carbamimidamido-5-acetamido-6-[methyl(propyl)carbamoyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 4-Acetyl-4-Guanidino-6-Methyl(Propyl)Carboxamide-4,5-Dihydro-2h-Pyran-2-Carboxylic Acid

Database IDs

• PubChem SID: 160966619; 46508580
• PubChem CID: 449379

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7997653
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.6801727
• LogD (pH = 7.4): -3.6731498
• Log P: -3.6731198
• Molar Refractivity: 95.3134 cm^3
• Polarizability: 32.36067 Å^3
• Polar Surface Area: 157.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.68
• LOG S: -2.83
• Solubility (Water): 5.03e-01 g/l

DETAILS

DrugBank - DB03503

Drug information: experimental