7-bromo-2-[2-(trideuteriomethoxy)phenyl]-5H-pyrazolo[4,3-c]quinolin-3-one

ID: ALA4094802

PubChem CID: 124111375

Max Phase: Preclinical

Molecular Formula: C17H12BrN3O2

Molecular Weight: 370.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [2H]C([2H])([2H])Oc1ccccc1-n1nc2c3ccc(Br)cc3[nH]cc-2c1=O

Standard InChI:  InChI=1S/C17H12BrN3O2/c1-23-15-5-3-2-4-14(15)21-17(22)12-9-19-13-8-10(18)6-7-11(13)16(12)20-21/h2-9,19H,1H3/i1D3

Standard InChI Key:  SMVMDVALPRQYTP-FIBGUPNXSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.5187  -19.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5175  -20.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2256  -20.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2238  -19.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9324  -19.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9358  -20.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6482  -20.6517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3617  -20.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6414  -19.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3549  -19.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9668  -18.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6315  -18.1091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8124  -18.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0389  -17.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8572  -17.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2655  -16.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8565  -15.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0351  -15.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6306  -16.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7662  -19.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8095  -20.6503    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.2654  -18.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0826  -18.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4908  -18.8192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4916  -17.4038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.8967  -18.1103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 14  1  0
 11 20  2  0
  2 21  1  0
 15 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  ISO  3  24   2  25   2  26   2
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: 370.21

Molecular Weight (Monoisotopic): 369.0113

AlogP: 3.59

#Rotatable Bonds: 2

Polar Surface Area: 59.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.43

CX Basic pKa: 1.28

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.91

References

1. Knutson DE, Kodali R, Divović B, Treven M, Stephen MR, Zahn NM, Dobričić V, Huber AT, Meirelles MA, Verma RS, Wimmer L, Witzigmann C, Arnold LA, Chiou LC, Ernst M, Mihovilovic MD, Savić MM, Sieghart W, Cook JM..  (2018)  Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability.,  61  (6): [PMID:29481759] [10.1021/acs.jmedchem.7b01664]

Source

Source(1):

• Scientific Literature