(R)-3-(2-Amino-1,3',3'-trimethyl-5-oxo-1,3',4',5-tetrahydro-2'H-spiro[imidazole-4,1'-naphthalene]-7'-yl)benzonitrile

ID: ALA2349468

Chembl Id: CHEMBL2349468

PubChem CID: 66683709

Max Phase: Preclinical

Molecular Formula: C22H22N4O

Molecular Weight: 358.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@]2(CC(C)(C)Cc3ccc(-c4cccc(C#N)c4)cc32)N=C1N

Standard InChI:  InChI=1S/C22H22N4O/c1-21(2)11-17-8-7-16(15-6-4-5-14(9-15)12-23)10-18(17)22(13-21)19(27)26(3)20(24)25-22/h4-10H,11,13H2,1-3H3,(H2,24,25)/t22-/m1/s1

Standard InChI Key:  KITXOXOZOIMSTQ-JOCHJYFZSA-N

Alternative Forms

1. Parent:

   

   ALA2349468

   3-[(8R)-2'-amino-1',6,6-trimethyl-5'-oxospiro[5,7-dihydronaphthalene-8,4'-imidazole]-2-yl]benzonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.45

Molecular Weight (Monoisotopic): 358.1794

AlogP: 3.18

#Rotatable Bonds: 1

Polar Surface Area: 82.48

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.43

CX LogP: 3.88

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -0.11

References

1. Hunt KW, Cook AW, Watts RJ, Clark CT, Vigers G, Smith D, Metcalf AT, Gunawardana IW, Burkard M, Cox AA, Geck Do MK, Dutcher D, Thomas AA, Rana S, Kallan NC, DeLisle RK, Rizzi JP, Regal K, Sammond D, Groneberg R, Siu M, Purkey H, Lyssikatos JP, Marlow A, Liu X, Tang TP..  (2013)  Spirocyclic β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors: from hit to lowering of cerebrospinal fluid (CSF) amyloid β in a higher species.,  56  (8): [PMID:23537249] [10.1021/jm4002154]

Source

Source(1):

• Scientific Literature