1-(3-chloro-4-(3-phenoxypropoxy)phenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine

ID: ALA1617293

PubChem CID: 280860

Max Phase: Preclinical

Molecular Formula: C20H24ClN5O2

Molecular Weight: 401.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)N=C(N)N=C(N)N1c1ccc(OCCCOc2ccccc2)c(Cl)c1

Standard InChI:  InChI=1S/C20H24ClN5O2/c1-20(2)25-18(22)24-19(23)26(20)14-9-10-17(16(21)13-14)28-12-6-11-27-15-7-4-3-5-8-15/h3-5,7-10,13H,6,11-12H2,1-2H3,(H4,22,23,24,25)

Standard InChI Key:  UTCUREXCXPTEBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -1.0147    1.9412    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4142    1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2721    1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436   -0.5338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -1.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726   -0.5338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581    0.7037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -1.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -1.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065   -2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5577    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4155    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4155   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0
  2 16  1  0
  2 20  1  0
  3 22  1  0
  3 23  1  0
  4  9  1  0
  4 10  1  0
  4 11  1  0
  5  9  1  0
  5 12  2  0
  6 11  2  0
  6 12  1  0
  7 11  1  0
  8 12  1  0
  9 17  1  0
  9 18  1  0
 10 13  1  0
 10 14  2  0
 13 15  2  0
 14 19  1  0
 15 16  1  0
 16 19  2  0
 20 21  1  0
 21 22  1  0
 23 24  2  0
 23 25  1  0
 24 26  1  0
 25 27  2  0
 26 28  2  0
 27 28  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1617293

   Ethanesulfonic acid,6-diamino-1-[3-chloro-4-(3-phenoxypropoxy)phenyl]-1,2-dihydro-2,2-dimethyl-s-triazine (1:1)

2. Parent:

   

   ALA1617293

   1-[3-Chloro-4-(3-phenoxypropoxy)phenyl]-6,6-dimethyl-1,3,5-triazine-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: 401.90

Molecular Weight (Monoisotopic): 401.1619

AlogP: 3.37

#Rotatable Bonds: 7

Polar Surface Area: 98.46

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.91

CX LogP: 3.25

CX LogD: 2.63

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.75

References

1. Srinivasan B, Tonddast-Navaei S, Skolnick J..  (2015)  Ligand binding studies, preliminary structure-activity relationship and detailed mechanistic characterization of 1-phenyl-6,6-dimethyl-1,3,5-triazine-2,4-diamine derivatives as inhibitors of Escherichia coli dihydrofolate reductase.,  103  [PMID:26414808] [10.1016/j.ejmech.2015.08.021]

Source

Source(1):

• Scientific Literature