6-[(2-Difluoromethoxy-phenylamino)-methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine

ID: ALA347088

PubChem CID: 472852

Max Phase: Preclinical

Molecular Formula: C16H16F2N6O

Molecular Weight: 346.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CNc2ccccc2OC(F)F)cnc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C16H16F2N6O/c1-8-9(7-22-14-12(8)13(19)23-16(20)24-14)6-21-10-4-2-3-5-11(10)25-15(17)18/h2-5,7,15,21H,6H2,1H3,(H4,19,20,22,23,24)

Standard InChI Key:  BKBLAMYQCCHEHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.9417   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -3.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -5.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -3.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -5.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -4.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -3.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -2.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -5.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -6.0125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -4.7667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  3  1  0
  7  1  1  0
  8  4  1  0
  9 14  1  0
 10 13  1  0
 11 10  1  0
 12 16  1  0
 13 15  2  0
 14  7  2  0
 15 12  1  0
 16  9  1  0
 17  5  1  0
 18  6  1  0
 19 11  1  0
 20 11  1  0
 21  8  1  0
 22 13  1  0
 23 15  1  0
 24 25  1  0
 25 23  2  0
  2  6  2  0
  9  8  2  0
 24 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA347088

   6-[(2-Difluoromethoxy-phenylamino)-methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine

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: 346.34

Molecular Weight (Monoisotopic): 346.1354

AlogP: 2.71

#Rotatable Bonds: 5

Polar Surface Area: 111.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.86

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -1.38

References

1. Debnath AK..  (2002)  Pharmacophore mapping of a series of 2,4-diamino-5-deazapteridine inhibitors of Mycobacterium avium complex dihydrofolate reductase.,  45  (1): [PMID:11754578] [10.1021/jm010360c]

Source

Source(1):

• Scientific Literature