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

ID: ALA132703

PubChem CID: 10637973

Max Phase: Preclinical

Molecular Formula: C17H24N4O

Molecular Weight: 300.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCOc1ccccc1Cc1cnc(N)nc1N

Standard InChI:  InChI=1S/C17H24N4O/c1-2-3-4-7-10-22-15-9-6-5-8-13(15)11-14-12-20-17(19)21-16(14)18/h5-6,8-9,12H,2-4,7,10-11H2,1H3,(H4,18,19,20,21)

Standard InChI Key:  LACLHRYBUASBLN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.9292   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -5.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -6.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -5.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -5.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -4.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -6.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -4.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -6.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -6.5000    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  2  1  0
 11  4  1  0
 12  9  1  0
 13  7  1  0
 14  9  1  0
 15 12  1  0
 16 15  1  0
 17 18  1  0
 18 19  1  0
 19 16  1  0
 20 13  2  0
 21 17  1  0
 22 20  1  0
  8  3  2  0
 22 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA132703

   5-[(2-Hexoxyphenyl)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: 300.41

Molecular Weight (Monoisotopic): 300.1950

AlogP: 3.19

#Rotatable Bonds: 8

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: 3.81

CX LogD: 3.63

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.33

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