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

ID: ALA3314360

PubChem CID: 118707560

Max Phase: Preclinical

Molecular Formula: C22H25ClN4O

Molecular Weight: 396.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1Cc2cc(CN(C)C)ccc2CN1C(=O)c1cc2cc(Cl)ncc2n1C

Standard InChI:  InChI=1S/C22H25ClN4O/c1-14-7-17-8-15(12-25(2)3)5-6-16(17)13-27(14)22(28)19-9-18-10-21(23)24-11-20(18)26(19)4/h5-6,8-11,14H,7,12-13H2,1-4H3

Standard InChI Key:  XFVPHPQDPXRAFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3152   -3.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -3.9273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288   -4.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0270   -2.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7424   -3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -3.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5287   -4.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0144   -3.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283   -2.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7839   -4.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8394   -3.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2521   -4.2231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2516   -2.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8346   -4.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2438   -5.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0727   -4.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4836   -4.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0692   -5.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4788   -6.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3026   -6.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7151   -5.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3031   -4.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7149   -7.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5399   -7.0815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9522   -7.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9526   -6.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006   -2.6876    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4181   -4.2168    0.0000 C   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
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  6  7  1  0
  7  8  1  0
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  9  5  1  0
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  8 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 12 16  1  0
 14 15  1  0
 15 18  1  0
 17 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
  1 27  1  0
 14 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3314360

   ---

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: 396.92

Molecular Weight (Monoisotopic): 396.1717

AlogP: 3.88

#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: 3.24

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -1.24

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