(4Z)-2-[(1S,2R)-1-amino-2-hydroxypropyl]-1-(2-hydroxyethyl)-4-(indol-3-ylmethylidene)-4,5-dihydro-1H-imidazol-5-one

• ChemBase ID: 1429
• Molecular Formular: C17H20N4O3
• Molecular Mass: 328.3657
• Monoisotopic Mass: 328.15354052
• SMILES: C[C@@H](O)[C@@H](N)C1=N/C(=C\c2c[nH]c3ccccc23)/C(=O)N1CCO
• Canonical SMILES: OCCN1C(=O)/C(=C/c2c[nH]c3c2cccc3)/N=C1[C@@H]([C@H](O)C)N
• InChI: InChI=1S/C17H20N4O3/c1-10(23)15(18)16-20-14(17(24)21(16)6-7-22)8-11-9-19-13-5-3-2-4-12(11)13/h2-5,8-10,15,19,22-23H,6-7,18H2,1H3/b14-8-/t10-,15-/m1/s1
• InChIKey: VFTCTFWPSJPJLY-RKHBVOJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4Z)-2-[(1S,2R)-1-amino-2-hydroxypropyl]-1-(2-hydroxyethyl)-4-(indol-3-ylmethylidene)-4,5-dihydro-1H-imidazol-5-one
• IUPAC Traditional name: (5Z)-2-[(1S,2R)-1-amino-2-hydroxypropyl]-3-(2-hydroxyethyl)-5-(indol-3-ylmethylidene)imidazol-4-one
• Synonyms: (5z)-5-(1h-Indol-3-Ylmethylene)-4h-Imidazol-4-One

Database IDs

• PubChem SID: 162103322
• PubChem CID: 17754110

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.700944
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.7090592
• LogD (pH = 7.4): -0.99048734
• Log P: -0.5996363
• Molar Refractivity: 89.6913 cm^3
• Polarizability: 35.592075 Å^3
• Polar Surface Area: 112.04 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.21
• LOG S: -3.23
• Solubility (Water): 1.91e-01 g/l

DETAILS

DrugBank - DB01653

Drug information: experimental