{6-[(Dimethylamino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl}[1-methyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]-methanone

ID: ALA3314356

PubChem CID: 118707557

Max Phase: Preclinical

Molecular Formula: C22H23F3N4O

Molecular Weight: 416.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc2c(c1)CCN(C(=O)c1cc3cc(C(F)(F)F)ncc3n1C)C2

Standard InChI:  InChI=1S/C22H23F3N4O/c1-27(2)12-14-4-5-16-13-29(7-6-15(16)8-14)21(30)18-9-17-10-20(22(23,24)25)26-11-19(17)28(18)3/h4-5,8-11H,6-7,12-13H2,1-3H3

Standard InChI Key:  VGJDJTDQWBICRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   16.2329   -7.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5066   -9.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2733   -8.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2311   -5.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7439   -9.8273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4556   -5.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5181   -6.6731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2767   -6.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0434   -6.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5071   -7.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7324   -5.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4479   -8.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6829   -9.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9464   -5.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9189   -9.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5192   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6877   -7.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9467   -6.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4561   -6.9689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2184   -6.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9880   -7.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1566   -9.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0386   -7.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8047   -5.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1562  -10.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7329   -6.9237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9191   -8.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0835   -5.8500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8045   -4.6005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0834   -5.0169    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 14  4  2  0
 19  8  1  0
 20  9  1  0
 13  2  2  0
 20 11  2  0
 19 23  1  0
  5 22  1  0
 27 10  2  0
 10 17  1  0
  2 27  1  0
  1 18  2  0
 14 18  1  0
  7  1  1  0
 15  5  1  0
 16 24  1  0
 18 26  1  0
  9 19  1  0
 26 20  1  0
  4 16  1  0
  5 25  1  0
 16  7  2  0
 17  8  1  0
  3 13  1  0
 23 12  1  0
 26 21  1  0
 17  3  2  0
 12  3  1  0
  2 15  1  0
  9  6  2  0
 11 14  1  0
 24 28  1  0
 24 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3314356

   ---

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: 416.45

Molecular Weight (Monoisotopic): 416.1824

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 41.37

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 3.27

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.60

References

1. Georgsson J, Bergström F, Nordqvist A, Watson MJ, Blundell CD, Johansson MJ, Petersson AU, Yuan ZQ, Zhou Y, Kristensson L, Kakol-Palm D, Tyrchan C, Wellner E, Bauer U, Brodin P, Svensson Henriksson A..  (2014)  GPR103 antagonists demonstrating anorexigenic activity in vivo: design and development of pyrrolo[2,3-c]pyridines that mimic the C-terminal Arg-Phe motif of QRFP26.,  57  (14): [PMID:24937104] [10.1021/jm401951t]

2. Georgsson, Jennie J and 15 more authors.  2014-07-24  GPR103 antagonists demonstrating anorexigenic activity in vivo: design and development of pyrrolo[2,3-c]pyridines that mimic the C-terminal Arg-Phe motif of QRFP26.  [PMID:24937104]

Source

Source(1):

• Scientific Literature