Ethyl 5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate

ID: ALA3317685

PubChem CID: 118708353

Max Phase: Preclinical

Molecular Formula: C23H21N5O2

Molecular Weight: 399.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c3cccnc3cc(CCc3nc4ccccc4n3C)n2n1

Standard InChI:  InChI=1S/C23H21N5O2/c1-3-30-23(29)19-14-21-16-7-6-12-24-18(16)13-15(28(21)26-19)10-11-22-25-17-8-4-5-9-20(17)27(22)2/h4-9,12-14H,3,10-11H2,1-2H3

Standard InChI Key:  KUGHRAHSLFOUTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    1.2406  -11.0772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315  -10.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -9.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406   -9.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -9.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547   -9.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -9.8514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638  -10.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547  -11.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456  -10.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702   -9.3036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -8.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254   -8.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486   -7.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -7.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8658   -7.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0729  -11.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0729  -11.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7778  -12.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251  -11.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730  -12.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644  -13.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660  -13.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730  -13.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902  -13.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2987  -13.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902  -12.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959  -11.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2744   -7.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0915   -7.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
 11 12  2  0
 12 13  1  0
  6 13  2  0
  7 11  1  0
 14 15  2  0
 14 16  1  0
 12 14  1  0
 17 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19 23  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 21 27  2  0
 22 24  2  0
 20 28  1  0
 18 19  1  0
  8 17  1  0
 29 30  1  0
 16 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3317685

   ---

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: 399.45

Molecular Weight (Monoisotopic): 399.1695

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 74.31

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.79

CX LogP: 3.88

CX LogD: 3.87

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.37

References

1. Dore A, Asproni B, Scampuddu A, Pinna GA, Christoffersen CT, Langgård M, Kehler J..  (2014)  Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors.,  84  [PMID:25016376] [10.1016/j.ejmech.2014.07.020]

Source

Source(1):

• Scientific Literature