7-(4-methoxybenzyl)-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-amine

ID: ALA1096531

PubChem CID: 46887915

Max Phase: Preclinical

Molecular Formula: C22H28N6O

Molecular Weight: 392.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CN2CCc3c(c(N4CCCCC4)nc4[nH]nc(N)c34)C2)cc1

Standard InChI:  InChI=1S/C22H28N6O/c1-29-16-7-5-15(6-8-16)13-27-12-9-17-18(14-27)22(28-10-3-2-4-11-28)24-21-19(17)20(23)25-26-21/h5-8H,2-4,9-14H2,1H3,(H3,23,24,25,26)

Standard InChI Key:  STUAUXQAFHHZTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    1.0438   -5.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -6.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -6.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -5.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747   -4.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -5.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439   -9.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8530  -10.1461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -8.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5721   -9.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8602   -9.3423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3763   -8.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239  -10.1297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -9.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948  -10.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778  -10.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853  -11.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120  -10.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1556   -8.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725   -8.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -7.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693   -7.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533   -7.6599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425   -8.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430   -7.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887   -3.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -3.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -9.9960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433   -7.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
 19  7  2  0
  7  8  1  0
  8 10  2  0
  9 20  2  0
  9 10  1  0
 11 12  2  0
 12  9  1  0
  7 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  2  1  0
  5 26  1  0
  1  6  2  0
 26 27  1  0
  1  2  1  0
  2  3  2  0
 12 29  1  0
 10 28  1  0
 28 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096531

   7-(4-methoxybenzyl)-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-amine

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: 392.51

Molecular Weight (Monoisotopic): 392.2325

AlogP: 3.10

#Rotatable Bonds: 4

Polar Surface Area: 83.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.77

CX LogP: 3.31

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -1.08

References

1. Guo C, Guzzo PR, Hadden M, Sargent BJ, Yet L, Kan Y, Palyha O, Kelly TM, Guan X, Rosko K, Gagen K, Metzger JM, Dragovic J, Lyons K, Lin LS, Nargund RP..  (2010)  Synthesis of 7-benzyl-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-ylamine and its analogs as bombesin receptor subtype-3 agonists.,  20  (9): [PMID:20371178] [10.1016/j.bmcl.2010.03.065]

Source

Source(1):

• Scientific Literature