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

ID: ALA44684

PubChem CID: 21147532

Max Phase: Preclinical

Molecular Formula: C20H24BrN5O7

Molecular Weight: 526.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H24BrN5O7/c1-32-13-7-10(6-11-9-24-20(23)26-18(11)22)8-14(17(13)21)33-5-4-15(27)25-12(19(30)31)2-3-16(28)29/h7-9,12H,2-6H2,1H3,(H,25,27)(H,28,29)(H,30,31)(H4,22,23,24,26)

Standard InChI Key:  LXVAIRRPWXYFBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.0417    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -2.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -3.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -4.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -0.4750    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -1.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    0.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -4.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    0.4333    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  2  0
  6 17  1  0
  7 16  2  0
  8  4  1  0
  9 13  1  0
 10 12  1  0
 11 14  1  0
 12 19  1  0
 10 13  1  0
 14  3  1  0
 15  8  2  0
 16 11  1  0
 17 11  2  0
 18 27  1  0
 19 31  1  0
 20  9  2  0
 21 12  2  0
 22 18  2  0
 23 13  1  0
 24  2  1  0
 25  4  1  0
 26  5  1  0
 27 23  1  0
 28  6  1  0
 29  9  1  0
 30  7  1  0
 31 28  1  0
 32 18  1  0
 33 30  1  0
  3 15  1  0
  5  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA44684

   2-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propionylamino}-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: 526.34

Molecular Weight (Monoisotopic): 525.0859

AlogP: 1.21

#Rotatable Bonds: 12

Polar Surface Area: 199.98

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.66

CX Basic pKa: 8.15

CX LogP: -0.84

CX LogD: -4.22

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.08

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