5-[4-Methoxy-3-(1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yloxy)-phenyl]-1-methyl-imidazolidin-2-one

ID: ALA2112410

PubChem CID: 71458008

Max Phase: Preclinical

Molecular Formula: C22H24N2O3

Molecular Weight: 364.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2CNC(=O)N2C)cc1O[C@@H]1CC2CC1c1ccccc12

Standard InChI:  InChI=1S/C22H24N2O3/c1-24-18(12-23-22(24)25)13-7-8-19(26-2)21(10-13)27-20-11-14-9-17(20)16-6-4-3-5-15(14)16/h3-8,10,14,17-18,20H,9,11-12H2,1-2H3,(H,23,25)/t14?,17?,18?,20-/m1/s1

Standard InChI Key:  CCNUQTMMRGAWTF-YETWJFQASA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   10.6212   -6.4868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3512   -7.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8489   -2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -2.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349   -3.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9072   -5.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4871   -7.3088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2728   -2.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0089   -1.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1691   -3.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9072   -5.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5570   -3.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3890   -1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2231   -6.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1691   -4.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8613   -7.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9072   -3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -4.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -3.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4374   -6.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9072   -2.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8948   -3.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5588   -2.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6572   -2.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1808   -3.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0187   -2.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4 14  1  0
  5 13  1  1
  6  3  1  0
  7  1  1  0
  8  2  1  0
  9  4  1  0
 10  3  1  0
 11 16  2  0
 12  7  1  0
 13 11  1  0
 14  5  1  0
 15  7  1  0
 16 12  1  0
 17  2  2  0
 18 20  2  0
 19 12  2  0
 20 19  1  0
 21  1  1  0
 22 18  1  0
 23  6  1  0
 24  9  1  0
 25 22  1  0
 26 23  2  0
 27 24  2  0
 15  8  1  0
 18 11  1  0
  4 10  1  0
  6  9  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112410

   5-[4-methoxy-3-[[(9R)-9-tricyclo[6.2.1.02,7]undeca-2,4,6-trienyl]oxy]phenyl]-1-methylimidazolidin-2-one

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: 364.45

Molecular Weight (Monoisotopic): 364.1787

AlogP: 3.81

#Rotatable Bonds: 4

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.62

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.90

Np Likeness Score: 0.52

References

1. Saccomano NA, Vinick FJ, Koe BK, Nielsen JA, Whalen WM, Meltz M, Phillips D, Thadieo PF, Jung S, Chapin DS..  (1991)  Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl]-2-imidazolidinones.,  34  (1): [PMID:1992129] [10.1021/jm00105a045]

Source

Source(1):

• Scientific Literature