3-Methyl-6-phenylsulfanyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrobromide

ID: ALA552736

PubChem CID: 12668037

Max Phase: Preclinical

Molecular Formula: C17H20BrNO2S

Molecular Weight: 301.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Br.CN1CCc2cc(O)c(O)c(Sc3ccccc3)c2CC1

Standard InChI:  InChI=1S/C17H19NO2S.BrH/c1-18-9-7-12-11-15(19)16(20)17(14(12)8-10-18)21-13-5-3-2-4-6-13;/h2-6,11,19-20H,7-10H2,1H3;1H

Standard InChI Key:  QNYLUARCYAZETH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    6.9412   -2.1051    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315   -0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580   -3.0236    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884    1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9404    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    1.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685   -1.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -3.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685    1.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -5.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528   -2.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4863   -3.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2967   -5.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -5.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  3  6  2  0
  2  7  1  0
  5  8  2  0
  6  8  1  0
  4 10  1  0
  5 11  1  0
  9 12  1  0
 10 12  1  0
  3 13  1  0
  9 14  1  0
 11 14  1  0
  7 15  1  0
  6 16  1  0
  9 17  1  0
 15 18  1  0
 15 19  2  0
 19 20  1  0
 18 21  2  0
 20 22  2  0
 21 22  1  0
M  END

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: 301.41

Molecular Weight (Monoisotopic): 301.1136

AlogP: 3.28

#Rotatable Bonds: 2

Polar Surface Area: 43.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: 7.96

CX LogP: 3.52

CX LogD: 3.08

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -0.08

References

1. Kaiser C, Ali FE, Bondinell WE, Brenner M, Holden KG, Ku TW, Oh HJ, Ross ST, Yim NC, Zirkle CL, Hahn RA, Sarau HM, Setler PE, Wardell JR..  (1980)  6-(Phenylthio)-substituted 2,3,4,5-tetrahydro-1H-3-benzazepines, a novel class of dopamine receptor antagonists and neuroleptics.,  23  (9): [PMID:6106062] [10.1021/jm00183a002]

Source

Source(1):

• Scientific Literature