N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-5-(5-fluoropyridin-3-yl)thiophene-2-carboxamide

ID: ALA2401999

PubChem CID: 59761433

Max Phase: Preclinical

Molecular Formula: C21H18FN3O2S

Molecular Weight: 395.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NC2CC2)cc1NC(=O)c1ccc(-c2cncc(F)c2)s1

Standard InChI:  InChI=1S/C21H18FN3O2S/c1-12-2-3-13(20(26)24-16-4-5-16)9-17(12)25-21(27)19-7-6-18(28-19)14-8-15(22)11-23-10-14/h2-3,6-11,16H,4-5H2,1H3,(H,24,26)(H,25,27)

Standard InChI Key:  GWAMNECAZIXYSS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.3559  -28.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6404  -28.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9274  -29.8129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9286  -28.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1406  -28.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6523  -29.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1379  -30.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6386  -27.7476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3522  -27.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0646  -27.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7777  -27.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7763  -26.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0559  -26.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3457  -26.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6283  -26.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4929  -27.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4943  -28.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2067  -27.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9220  -27.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3326  -28.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7439  -27.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8847  -30.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0759  -31.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8193  -31.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3705  -32.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1815  -32.2422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4342  -31.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0119  -31.9700    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  4  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 11 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 20 19  1  0
 21 20  1  0
 19 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  7 22  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2401999

   N-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-5-(5-fluoropyridin-3-yl)thiophene-2-carboxamide

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: 395.46

Molecular Weight (Monoisotopic): 395.1104

AlogP: 4.40

#Rotatable Bonds: 5

Polar Surface Area: 71.09

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: 1.98

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -1.91

References

1. Wrobleski ST, Lin S, Dhar TG, Dyckman AJ, Li T, Pitt S, Zhang R, Fan Y, Doweyko AM, Tokarski JS, Kish KF, Kiefer SE, Sack JS, Newitt JA, Witmer MR, McKinnon M, Barrish JC, Dodd JH, Schieven GL, Leftheris K..  (2013)  The identification of novel p38α isoform selective kinase inhibitors having an unprecedented p38α binding mode.,  23  (14): [PMID:23746475] [10.1016/j.bmcl.2013.05.047]

Source

Source(1):

• Scientific Literature