8-Methoxy-3-(4-phenylbutyl)-1-vinyl-2,3,4,5-tetrahydro-1H-3-benzazepine

ID: ALA4065052

PubChem CID: 137633889

Max Phase: Preclinical

Molecular Formula: C23H29NO

Molecular Weight: 335.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H29NO/c1-3-20-18-24(15-8-7-11-19-9-5-4-6-10-19)16-14-21-12-13-22(25-2)17-23(20)21/h3-6,9-10,12-13,17,20H,1,7-8,11,14-16,18H2,2H3

Standard InChI Key:  RELAUZJYSYSZPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.5677   -8.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3091   -8.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4875   -9.7181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1393  -10.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9653  -10.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6305   -9.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8240   -8.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2255   -8.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4334   -8.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2430   -9.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8428   -9.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5769   -7.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2900   -9.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5254  -10.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3279  -10.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8949  -10.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -10.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9287  -11.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7304  -11.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2982  -10.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0591  -10.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2579   -9.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8671   -7.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8337   -7.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0245   -7.1930    0.0000 C   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
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4065052

   ---

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: 335.49

Molecular Weight (Monoisotopic): 335.2249

AlogP: 4.85

#Rotatable Bonds: 7

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.90

CX LogP: 5.49

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -0.12

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