5-(2,3,4-Trimethoxy-benzyl)-pyrimidine-2,4-diamine

ID: ALA336420

Cas Number: 6981-04-0

PubChem CID: 10755919

Max Phase: Preclinical

Molecular Formula: C14H18N4O3

Molecular Weight: 290.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2cnc(N)nc2N)c(OC)c1OC

Standard InChI:  InChI=1S/C14H18N4O3/c1-19-10-5-4-8(11(20-2)12(10)21-3)6-9-7-17-14(16)18-13(9)15/h4-5,7H,6H2,1-3H3,(H4,15,16,17,18)

Standard InChI Key:  LMDWIFOXRXQEPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    8.1250   -4.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -5.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -3.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -5.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -3.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  6  1  0
  5  1  1  0
  6  7  2  0
  7  9  1  0
  8  5  2  0
  9  3  1  0
 10  8  1  0
 11 13  1  0
 12  7  1  0
 13 12  2  0
 14  2  1  0
 15  5  1  0
 16  4  1  0
 17  6  1  0
 18 11  1  0
 19 16  1  0
 20 17  1  0
 21 18  1  0
 10  3  2  0
 11  4  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA336420

   2,4-Pyrimidinediamine, 5-[(2,3,4-trimethoxypheny

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: 290.32

Molecular Weight (Monoisotopic): 290.1379

AlogP: 1.26

#Rotatable Bonds: 5

Polar Surface Area: 105.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.14

CX LogP: 1.28

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.85

Np Likeness Score: 0.08

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