methyl (4,6-diamino-2-(1-((3-fluorothiophen-2-yl)methyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(ethyl)carbamate

ID: ALA4554294

PubChem CID: 155556617

Max Phase: Preclinical

Molecular Formula: C19H19FN8O2S

Molecular Weight: 442.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(C(=O)OC)c1c(N)nc(-c2nn(Cc3sccc3F)c3ncccc23)nc1N

Standard InChI:  InChI=1S/C19H19FN8O2S/c1-3-27(19(29)30-2)14-15(21)24-17(25-16(14)22)13-10-5-4-7-23-18(10)28(26-13)9-12-11(20)6-8-31-12/h4-8H,3,9H2,1-2H3,(H4,21,22,24,25)

Standard InChI Key:  KHDVQTVODOJVBV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   24.3577  -11.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1749  -11.4848    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.4293  -10.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7663  -10.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1076  -10.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4643  -12.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4632  -13.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1712  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1694  -12.5712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8780  -12.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8829  -13.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6672  -14.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1472  -13.3806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6594  -12.7176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6531  -11.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9243  -14.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3793  -15.4353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6358  -16.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4369  -16.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9810  -15.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7216  -14.9882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6950  -17.1516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4955  -17.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7536  -18.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0379  -16.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8385  -16.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0922  -16.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7819  -15.9233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3303  -10.4559    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.1525  -17.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3520  -17.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 14 15  1  0
 15  1  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 12 16  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 18 27  1  0
 20 28  1  0
  5 29  1  0
 22 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554294

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 442.48

Molecular Weight (Monoisotopic): 442.1336

AlogP: 2.89

#Rotatable Bonds: 5

Polar Surface Area: 138.07

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.50

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -1.66

References

1. Li L, Zhang W, Lin F, Lu X, Chen W, Li X, Zhou X, Su R, Wang L, Zheng Z, Li S..  (2019)  Synthesis and biological evaluation of pyrazolo[3,4-b]pyridine-3-yl pyrimidine derivatives as sGC stimulators for the treatment of pulmonary hypertension.,  173  [PMID:30995566] [10.1016/j.ejmech.2019.04.014]

Source

Source(1):

• Scientific Literature