5-(2-Benzyloxy-benzyl)-pyrimidine-2,4-diamine

ID: ALA135854

PubChem CID: 10494869

Max Phase: Preclinical

Molecular Formula: C18H18N4O

Molecular Weight: 306.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncc(Cc2ccccc2OCc2ccccc2)c(N)n1

Standard InChI:  InChI=1S/C18H18N4O/c19-17-15(11-21-18(20)22-17)10-14-8-4-5-9-16(14)23-12-13-6-2-1-3-7-13/h1-9,11H,10,12H2,(H4,19,20,21,22)

Standard InChI Key:  ABJYILXBTKBIBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.1500   -5.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -5.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -5.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -6.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -4.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -4.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -6.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -5.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -6.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  3  1  0
  7  6  1  0
  8  5  1  0
  9  7  2  0
 10  9  1  0
 11  2  1  0
 12  4  1  0
 13 10  1  0
 14 13  1  0
 15  7  1  0
 16  9  1  0
 17 14  2  0
 18 14  1  0
 19 15  2  0
 20 19  1  0
 21 18  2  0
 22 17  1  0
 23 21  1  0
  8  3  2  0
 20 16  2  0
 23 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA135854

   5-[(2-Phenylmethoxyphenyl)methyl]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: 306.37

Molecular Weight (Monoisotopic): 306.1481

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 87.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.15

CX LogP: 3.32

CX LogD: 3.14

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.50

References

1. Selassie CD, Gan WX, Kallander LS, Klein TE..  (1998)  Quantitative structure-activity relationships of 2, 4-diamino-5-(2-X-benzyl)pyrimidines versus bacterial and avian dihydrofolate reductase.,  41  (22): [PMID:9784101] [10.1021/jm970776j]

Source

Source(1):

• Scientific Literature