(S)-N-(3-(2-amino-6-(fluoromethyl)-4-methyl-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-3-methylpyrazine-2-carboxamide

ID: ALA5285805

Max Phase: Preclinical

Molecular Formula: C19H19F2N5O3

Molecular Weight: 403.39

Names and Identifiers

Canonical SMILES:  COc1cnc(C(=O)Nc2ccc(F)c([C@]3(C)C=C(CF)OC(N)=N3)c2)c(C)n1

Standard InChI:  InChI=1S/C19H19F2N5O3/c1-10-16(23-9-15(24-10)28-3)17(27)25-11-4-5-14(21)13(6-11)19(2)7-12(8-20)29-18(22)26-19/h4-7,9H,8H2,1-3H3,(H2,22,26)(H,25,27)/t19-/m0/s1

Standard InChI Key:  VYZICWXJOCPCSB-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.0715   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -1.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860    0.8282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025    1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -0.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6416    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.0003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -1.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981   -1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.2375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  3  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 19 18  1  1
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 19  1  0
 18 29  1  0
 29 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285805

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 403.39

Molecular Weight (Monoisotopic): 403.1456

AlogP: 2.60

#Rotatable Bonds: 5

Polar Surface Area: 111.72

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.83

CX Basic pKa: 5.57

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.79

Np Likeness Score: -0.90

References

1. Oguma T, Uehara S, Nakahara K, Okuyama Y, Fuchino K, Suzuki N, Kan Y, Kanegawa N, Ogata Y, Kusakabe KI..  (2023)  A Quantum Mechanics-Based Method to Predict Intramolecular Hydrogen Bond Formation Reflecting P-glycoprotein Recognition.,  14  (2.0): [PMID:36793434] [10.1021/acsmedchemlett.2c00427]

Source

Source(1):

• Scientific Literature