[8-Methoxy-3-(4-phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]methanol

ID: ALA4088218

PubChem CID: 137644402

Max Phase: Preclinical

Molecular Formula: C22H29NO2

Molecular Weight: 339.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)C(CO)CN(CCCCc1ccccc1)CC2

Standard InChI:  InChI=1S/C22H29NO2/c1-25-21-11-10-19-12-14-23(16-20(17-24)22(19)15-21)13-6-5-9-18-7-3-2-4-8-18/h2-4,7-8,10-11,15,20,24H,5-6,9,12-14,16-17H2,1H3

Standard InChI Key:  WCPYKHQMSBMCQY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.3136   -6.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0550   -7.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2334   -8.1056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8851   -8.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7111   -8.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3763   -8.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5698   -7.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9714   -6.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1792   -6.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9888   -7.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5887   -8.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3228   -6.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0359   -8.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2713   -9.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0738   -9.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6407   -8.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4432   -8.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6745   -9.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4762   -9.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0441   -9.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8049   -8.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0037   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6130   -5.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5795   -6.3832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7703   -5.5806    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  1  0
  9 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088218

   ---

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: 339.48

Molecular Weight (Monoisotopic): 339.2198

AlogP: 3.65

#Rotatable Bonds: 7

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.48

CX LogP: 3.96

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.16

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