1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-1,4-diazepane

ID: ALA3819109

PubChem CID: 59485132

Max Phase: Preclinical

Molecular Formula: C25H34N2O2

Molecular Weight: 394.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2CCCN(c3c(C)c(C)c4c(c3C)CC(C)(C)O4)CC2)cc1

Standard InChI:  InChI=1S/C25H34N2O2/c1-17-18(2)24-22(16-25(4,5)29-24)19(3)23(17)27-13-7-12-26(14-15-27)20-8-10-21(28-6)11-9-20/h8-11H,7,12-16H2,1-6H3

Standard InChI Key:  MNIRCDLPWYWKRW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.7138   -1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    2.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    1.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -1.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8689    0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3032    1.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225    2.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8543    2.4896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    4.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1071    3.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3511    2.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1318    1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6315    1.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3534    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5758    3.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0761    3.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8539    2.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4299    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  6 10  1  0
  8 11  1  0
  9 12  1  0
  2 13  1  0
  2 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 17 19  1  0
 18 20  1  0
 19 21  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3819109

   1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)-1,4-diazepane

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: 394.56

Molecular Weight (Monoisotopic): 394.2620

AlogP: 5.05

#Rotatable Bonds: 3

Polar Surface Area: 24.94

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.13

CX LogP: 5.84

CX LogD: 5.82

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.36

References

1. Wakabayashi T, Tokunaga N, Tokumaru K, Ohra T, Koyama N, Hayashi S, Yamada R, Shirasaki M, Inui Y, Tsukamoto T..  (2016)  Discovery of Benzofuran Derivatives that Collaborate with Insulin-Like Growth Factor 1 (IGF-1) to Promote Neuroprotection.,  59  (10): [PMID:27163512] [10.1021/acs.jmedchem.6b00191]

Source

Source(1):

• Scientific Literature