(3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxyhex-1-yn-1-yl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 3389
• Molecular Formular: C20H20FN3O4
• Molecular Mass: 385.3889032
• Monoisotopic Mass: 385.14378436
• SMILES: Fc1c(C#C[C@@H](O)[C@@H](N)[C@H](O)C)c2c(NC(=O)/C/2=C\c2c(OC)cc[nH]2)cc1
• Canonical SMILES: COc1cc[nH]c1/C=C/1\C(=O)Nc2c1c(C#C[C@H]([C@H]([C@H](O)C)N)O)c(cc2)F
• InChI: InChI=1S/C20H20FN3O4/c1-10(25)19(22)16(26)6-3-11-13(21)4-5-14-18(11)12(20(27)24-14)9-15-17(28-2)7-8-23-15/h4-5,7-10,16,19,23,25-26H,22H2,1-2H3,(H,24,27)/b12-9-/t10-,16-,19+/m1/s1
• InChIKey: RAKYKJWUUUKCCW-MPLBGYFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxyhex-1-yn-1-yl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: (3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxyhex-1-yn-1-yl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
• Synonyms: 4-((3r,4s,5r)-4-Amino-3,5-Dihydroxy-Hex-1-Ynyl)-5-Fluoro-3-[1-(3-Methoxy-1h-Pyrrol-2-Yl)-Meth-(Z)-Ylidene]-1,3-Dihydro-Indol-2-One

Database IDs

• PubChem SID: 46505468; 160966830
• PubChem CID: 5288222

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.319682
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -1.873055
• LogD (pH = 7.4): -0.49746713
• Log P: 1.0056636
• Molar Refractivity: 101.4963 cm^3
• Polarizability: 38.46176 Å^3
• Polar Surface Area: 120.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.33
• LOG S: -4.28
• Solubility (Water): 2.01e-02 g/l

DETAILS

DrugBank - DB03737

Drug information: experimental