5-(4-chlorophenyl)-6-(1-(5-(diethylamino)pentan-2-ylamino)ethyl)pyrimidine-2,4-diamine

ID: ALA3272938

PubChem CID: 90677863

Max Phase: Preclinical

Molecular Formula: C21H33ClN6

Molecular Weight: 404.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCC(C)NC(C)c1nc(N)nc(N)c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H33ClN6/c1-5-28(6-2)13-7-8-14(3)25-15(4)19-18(20(23)27-21(24)26-19)16-9-11-17(22)12-10-16/h9-12,14-15,25H,5-8,13H2,1-4H3,(H4,23,24,26,27)

Standard InChI Key:  IQLAPNNGZXAPIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.6622  -13.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3784  -13.5257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3929  -14.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6933  -14.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792  -14.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626  -13.5521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796  -14.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633  -14.3968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941  -15.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7100  -15.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4241  -15.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4407  -16.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411  -17.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0249  -16.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0104  -16.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578  -18.0321    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1092  -14.7363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455  -12.3116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634  -14.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786  -15.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482  -14.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786  -16.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1939  -16.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939  -17.2960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092  -18.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787  -16.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092  -18.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787  -17.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  5  7  1  0
  7  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
  4 10  1  0
  3 17  1  0
  1 18  1  0
  8 19  1  0
 19 20  1  0
 19 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 25 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3272938

   5-(4-Chlorophenyl)-6-[1-[5-(diethylamino)pentan-2-ylamino]ethyl]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: 404.99

Molecular Weight (Monoisotopic): 404.2455

AlogP: 4.12

#Rotatable Bonds: 10

Polar Surface Area: 93.09

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.35

CX LogP: 3.85

CX LogD: -0.69

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.91

References

1. Ress RW, Chai SY, Winkley MW, Russell RB..  (1976)  Antimalarial activity of some novel derivatives of 2,4-diamino-5(p-chlorophenyl)-6-ethylpyrimidine (pyrimethamine).,  19  (5): [PMID:775088] [10.1021/jm00227a029]

Source

Source(1):

• Scientific Literature