3-(4-Phenylbutyl)-5-vinyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol

ID: ALA4075349

PubChem CID: 137652268

Max Phase: Preclinical

Molecular Formula: C22H27NO

Molecular Weight: 321.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC1CN(CCCCc2ccccc2)CCc2ccc(O)cc21

Standard InChI:  InChI=1S/C22H27NO/c1-2-19-17-23(14-7-6-10-18-8-4-3-5-9-18)15-13-20-11-12-21(24)16-22(19)20/h2-5,8-9,11-12,16,19,24H,1,6-7,10,13-15,17H2

Standard InChI Key:  IDWUXOVPWAEEOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.3719   -7.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1133   -7.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2917   -8.7598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9435   -9.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7695   -9.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4347   -8.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6282   -7.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0297   -7.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2375   -7.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0470   -8.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6470   -8.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3811   -6.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0941   -8.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3296   -9.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1321   -9.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6991   -9.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5016   -9.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7329  -10.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5344  -10.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1024   -9.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8633   -9.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0621   -8.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6713   -6.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6379   -7.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  2  1  0
  2  3  1  0
  6  4  1  0
  3  5  1  0
  4  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 12 23  2  0
  9 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4075349

   ---

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: 321.46

Molecular Weight (Monoisotopic): 321.2093

AlogP: 4.54

#Rotatable Bonds: 6

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.37

CX Basic pKa: 10.23

CX LogP: 4.59

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.22

References

1. Rath S, Schepmann D, Wünsch B..  (2017)  Replacement of benzylic hydroxy group by vinyl or hydroxymethyl moiety at the 3-benzazepine scaffold retaining GluN2B affinity.,  25  (20): [PMID:28797770] [10.1016/j.bmc.2017.07.059]

Source

Source(1):

• Scientific Literature