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

ID: ALA3314357

PubChem CID: 118707558

Max Phase: Preclinical

Molecular Formula: C27H28N4O

Molecular Weight: 424.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc2c(c1)CCN(C(=O)c1cc3cc(-c4ccccc4)ncc3n1C)C2

Standard InChI:  InChI=1S/C27H28N4O/c1-29(2)17-19-9-10-22-18-31(12-11-21(22)13-19)27(32)25-15-23-14-24(20-7-5-4-6-8-20)28-16-26(23)30(25)3/h4-10,13-16H,11-12,17-18H2,1-3H3

Standard InChI Key:  AOOWUKRCTFDBNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   16.2249   -7.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4961   -9.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2633   -8.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2231   -5.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7328   -9.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4461   -5.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5105   -6.6698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2667   -6.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0341   -6.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4966   -7.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7236   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4383   -8.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6728   -9.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9381   -5.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9082   -9.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5116   -5.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6775   -7.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9384   -6.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4466   -6.9655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2095   -6.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9791   -7.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1453   -9.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0292   -7.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7974   -5.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1449  -10.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7241   -6.9203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9084   -8.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7972   -4.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0761   -4.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3553   -4.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3555   -5.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0765   -5.8471    0.0000 C   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 32  2  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3314357

   ---

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: 424.55

Molecular Weight (Monoisotopic): 424.2263

AlogP: 4.50

#Rotatable Bonds: 4

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: 4.03

CX LogD: 2.63

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -1.44

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