Methyl 5-(((6-Amino-3,5-dicyano-4-(furan-2-yl)pyridin-2-yl)sulfanyl)methyl)furan-2-carboxylate

ID: ALA4547699

PubChem CID: 155553292

Max Phase: Preclinical

Molecular Formula: C18H12N4O4S

Molecular Weight: 380.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(CSc2nc(N)c(C#N)c(-c3ccco3)c2C#N)o1

Standard InChI:  InChI=1S/C18H12N4O4S/c1-24-18(23)14-5-4-10(26-14)9-27-17-12(8-20)15(13-3-2-6-25-13)11(7-19)16(21)22-17/h2-6H,9H2,1H3,(H2,21,22)

Standard InChI Key:  IYHVFAWVQMTRPT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.1047  -26.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1036  -27.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8116  -27.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5213  -27.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5185  -26.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8098  -25.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8074  -24.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2224  -25.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9286  -25.3641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8144  -28.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8142  -29.0502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3956  -27.4189    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6882  -27.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9801  -27.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2302  -27.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3169  -28.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1165  -28.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5240  -27.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9762  -27.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2373  -27.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6900  -27.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0981  -28.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8975  -28.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8716  -27.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4668  -26.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4592  -28.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6420  -28.3907    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  2  0
  6  1  1  0
  6  7  1  0
  8  9  3  0
  5  8  1  0
 10 11  3  0
  3 10  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
  4 15  1  0
 14 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 14  2  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547699

   ---

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: 380.39

Molecular Weight (Monoisotopic): 380.0579

AlogP: 3.34

#Rotatable Bonds: 5

Polar Surface Area: 139.07

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -1.70

References

1. Betti M, Catarzi D, Varano F, Falsini M, Varani K, Vincenzi F, Pasquini S, di Cesare Mannelli L, Ghelardini C, Lucarini E, Dal Ben D, Spinaci A, Bartolucci G, Menicatti M, Colotta V..  (2019)  Modifications on the Amino-3,5-dicyanopyridine Core To Obtain Multifaceted Adenosine Receptor Ligands with Antineuropathic Activity.,  62  (15): [PMID:31306001] [10.1021/acs.jmedchem.9b00106]

Source

Source(1):

• Scientific Literature