N-(5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)-7-formyl-6-((N-methylacetamido)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

ID: ALA4784243

PubChem CID: 118036192

Max Phase: Preclinical

Molecular Formula: C23H26N6O5

Molecular Weight: 466.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCOc1cc(NC(=O)N2CCCc3cc(CN(C)C(C)=O)c(C=O)nc32)ncc1C#N

Standard InChI:  InChI=1S/C23H26N6O5/c1-15(31)28(2)13-17-9-16-5-4-6-29(22(16)26-19(17)14-30)23(32)27-21-10-20(34-8-7-33-3)18(11-24)12-25-21/h9-10,12,14H,4-8,13H2,1-3H3,(H,25,27,32)

Standard InChI Key:  LKLLFMPSJSCSDN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   14.4356   -8.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4345   -9.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1425   -9.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1407   -7.7837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8494   -8.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8501   -9.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5587   -9.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2669   -9.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2622   -8.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5531   -7.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7278   -7.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7276   -6.9669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5487   -6.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2543   -6.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8389   -6.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8345   -5.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5414   -5.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5374   -4.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8270   -4.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1191   -4.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1266   -5.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8219   -3.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8165   -2.4781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7277   -9.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0205   -9.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3115   -9.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231   -8.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6051   -9.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3089  -10.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2431   -4.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9528   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6585   -4.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3682   -4.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0739   -4.0904    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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
  1 11  1  0
 11 12  2  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  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
 22 23  3  0
 19 22  1  0
 24 25  1  0
  2 24  1  0
 25 26  1  0
 25 27  1  0
 26 28  1  0
 26 29  2  0
 18 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4784243

   6-[[acetyl(methyl)amino]methyl]-N-[5-cyano-4-(2-methoxyethoxy)pyridin-2-yl]-7-formyl-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide

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: 466.50

Molecular Weight (Monoisotopic): 466.1965

AlogP: 2.15

#Rotatable Bonds: 8

Polar Surface Area: 137.75

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.87

CX Basic pKa: 2.20

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -1.40

References

1. Fairhurst RA,Knoepfel T,Buschmann N,Leblanc C,Mah R,Todorov M,Nimsgern P,Ripoche S,Niklaus M,Warin N,Luu VH,Madoerin M,Wirth J,Graus-Porta D,Weiss A,Kiffe M,Wartmann M,Kinyamu-Akunda J,Sterker D,Stamm C,Adler F,Buhles A,Schadt H,Couttet P,Blank J,Galuba I,Trappe J,Voshol J,Ostermann N,Zou C,Berghausen J,Del Rio Espinola A,Jahnke W,Furet P.  (2020)  Discovery of Roblitinib (FGF401) as a Reversible-Covalent Inhibitor of the Kinase Activity of Fibroblast Growth Factor Receptor 4.,  63  (21.0): [PMID:32930584] [10.1021/acs.jmedchem.0c01019]

Source

Source(1):

• Scientific Literature