(1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

• ChemBase ID: 5112
• Molecular Formular: C18H25N3O2
• Molecular Mass: 315.41
• Monoisotopic Mass: 315.19467706
• SMILES: [C@@]12([C@@H](C(=O)N3[C@@H]4[C@@H](C4)C[C@H]3C#N)N)C[C@]3(C[C@H](C[C@H](C3)C2)C1)O
• Canonical SMILES: N#C[C@@H]1C[C@H]2[C@@H](N1C(=O)[C@H]([C@]13C[C@@H]4C[C@H](C1)C[C@](C3)(C4)O)N)C2
• InChI: InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10-,11+,12-,13+,14+,15-,17+,18-/m1/s1
• InChIKey: QGJUIPDUBHWZPV-YQBUGCKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• IUPAC Traditional name: (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• Synonyms: (1S,3S,5S)-2-{(2S)-2-amino-2-[(1R,3S,5R,7S)-3-hydroxytricyclo[3.3.1.1~3,7~]dec-1-yl]acetyl}-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Database IDs

• PubChem SID: 99443936; 160968542
• PubChem CID: 11235729

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.743205
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.388905
• LogD (pH = 7.4): -0.6962074
• Log P: -0.079534434
• Molar Refractivity: 83.9913 cm^3
• Polarizability: 33.454536 Å^3
• Polar Surface Area: 90.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.88
• LOG S: -2.14
• Solubility (Water): 2.26e+00 g/l

DETAILS

DrugBank - DB07465

Drug information: experimental