2-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propyl}-pentanedioic acid

ID: ALA296525

PubChem CID: 2440

Max Phase: Preclinical

Molecular Formula: C20H25BrN4O6

Molecular Weight: 497.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc(OCCCC(CCC(=O)O)C(=O)O)c1Br

Standard InChI:  InChI=1S/C20H25BrN4O6/c1-30-14-8-11(7-13-10-24-20(23)25-18(13)22)9-15(17(14)21)31-6-2-3-12(19(28)29)4-5-16(26)27/h8-10,12H,2-7H2,1H3,(H,26,27)(H,28,29)(H4,22,23,24,25)

Standard InChI Key:  SZAVCZNFKJSWRN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    5.3375   -0.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9417   -3.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -5.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500    0.5583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -1.2292    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -4.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9625   -0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -1.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -4.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  6  1  0
  6 14  2  0
  7 13  1  0
  8  4  1  0
  9 11  1  0
 10 19  1  0
 11  3  1  0
 12  8  2  0
 13  9  2  0
 14  9  1  0
 15 23  1  0
 16 10  2  0
 17 15  2  0
 18  2  1  0
 19 28  1  0
 20  4  1  0
 21  5  1  0
 22 19  1  0
 23 22  1  0
 24 10  1  0
 25  6  1  0
 26  7  1  0
 27 15  1  0
 28 31  1  0
 29 26  1  0
 30 25  1  0
 31 29  1  0
  3 12  1  0
  5  7  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA296525

   2-[3-[2-Bromo-5-[(2,4-diaminopyrimidin-5-yl)methyl]-3-methoxy-phenoxy]propyl]pentanedioic acid

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: 497.35

Molecular Weight (Monoisotopic): 496.0957

AlogP: 2.73

#Rotatable Bonds: 12

Polar Surface Area: 170.88

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.05

CX Basic pKa: 8.15

CX LogP: 1.03

CX LogD: -2.47

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: 0.24

References

1. Birdsall B, Feeney J, Pascual C, Roberts GC, Kompis I, Then RL, Müller K, Kroehn A..  (1984)  A 1H NMR study of the interactions and conformations of rationally designed brodimoprim analogues in complexes with Lactobacillus casei dihydrofolate reductase.,  27  (12): [PMID:6438320] [10.1021/jm00378a025]

Source

Source(1):

• Scientific Literature