1-benzyl-3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

ID: ALA4205783

Cas Number: 851373-91-6

PubChem CID: 11151899

Product Number: J611257, Order Now?

Max Phase: Phase

Molecular Formula: C20H20ClN3

Molecular Weight: 337.85

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): Jnj-18038683

Canonical SMILES:  Clc1ccc(-c2nn(Cc3ccccc3)c3c2CCNCC3)cc1

Standard InChI:  InChI=1S/C20H20ClN3/c21-17-8-6-16(7-9-17)20-18-10-12-22-13-11-19(18)24(23-20)14-15-4-2-1-3-5-15/h1-9,22H,10-14H2

Standard InChI Key:  UKJPMZGILXATGT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    7.8858   -6.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5383   -6.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8967   -5.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6834   -7.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6922   -5.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3264   -5.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3265   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1026   -6.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5821   -6.0952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1024   -5.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0952   -4.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8049   -4.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7981   -3.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0830   -2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3733   -3.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3836   -4.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0952   -7.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7992   -7.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7867   -8.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4898   -9.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2022   -8.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2070   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5033   -7.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0748   -2.1570    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  3  5  1  0
  4  7  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205783

   JNJ-18038683

2. Alternative Forms:

   

   ALA4205783

   JNJ-18038683

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.85

Molecular Weight (Monoisotopic): 337.1346

AlogP: 3.94

#Rotatable Bonds: 3

Polar Surface Area: 29.85

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.90

CX LogP: 4.34

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -1.26

References

1. Modica MN, Lacivita E, Intagliata S, Salerno L, Romeo G, Pittalà V, Leopoldo M..  (2018)  Structure-Activity Relationships and Therapeutic Potentials of 5-HT7 Receptor Ligands: An Update.,  61  (19): [PMID:29767995] [10.1021/acs.jmedchem.7b01898]

2. Thirumaran SL, Lepailleur A, Rochais C..  (2019)  Structure-activity relationships of serotonin 5-HT₇ receptors ligands: A review.,  183  [PMID:31581003] [10.1016/j.ejmech.2019.111705]

3. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

4. Dvorak CA,Rudolph DA,Nepomuceno D,Dvorak L,Lord B,Fraser I,Bonaventure P,Lovenberg T,Carruthers NI.  (2021)  Discovery and SAR studies of 2-alkyl-3-phenyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepines as 5-HT inhibitors leading to the identification of a clinical candidate.,  31  [PMID:33171218] [10.1016/j.bmcl.2020.127669]

5. Kucwaj-Brysz K, Baltrukevich H, Czarnota K, Handzlik J..  (2021)  Chemical update on the potential for serotonin 5-HT₆ and 5-HT₇ receptor agents in the treatment of Alzheimer's disease.,  49  [PMID:34311086] [10.1016/j.bmcl.2021.128275]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data