2-{4-[2-(2,4-Diamino-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA124631

PubChem CID: 13912572

Max Phase: Preclinical

Molecular Formula: C21H22N6O5

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(CCc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)cnc2n1

Standard InChI:  InChI=1S/C21H22N6O5/c22-17-14-9-12(10-24-18(14)27-21(23)26-17)2-1-11-3-5-13(6-4-11)19(30)25-15(20(31)32)7-8-16(28)29/h3-6,9-10,15H,1-2,7-8H2,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,24,26,27)

Standard InChI Key:  RGUQKUKRLMXLCM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.9042   -0.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -4.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0292   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -4.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -5.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7417   -5.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    0.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -1.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -6.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0250   -6.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  2  1  0
  4  5  1  0
  5  1  2  0
  6  1  1  0
  7 12  1  0
  8  3  1  0
  9  7  1  0
 10 11  1  0
 11  9  1  0
 12 21  1  0
 13  4  1  0
 14 25  1  0
 15  7  2  0
 16 10  2  0
 17 14  2  0
 18  5  1  0
 19  6  1  0
 20 11  1  0
 21 30  2  0
 22 29  1  0
 23  8  2  0
 24 13  2  0
 25 20  1  0
 26 10  1  0
 27 32  1  0
 28 14  1  0
 29 27  2  0
 30 27  1  0
 31 24  1  0
 32 31  1  0
  4  3  2  0
 23 24  1  0
 22 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA124631

   2-{4-[2-(2,4-Diamino-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-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: 438.44

Molecular Weight (Monoisotopic): 438.1652

AlogP: 1.02

#Rotatable Bonds: 9

Polar Surface Area: 194.41

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.57

CX Basic pKa: 3.44

CX LogP: 1.02

CX LogD: -5.08

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.19

References

1. Piper JR, DeGraw JI, Colwell WT, Johnson CA, Smith RL, Waud WR, Sirotnak FM..  (1997)  Analogues of methotrexate in rheumatoid arthritis. 2. Effects of 5-deazaaminopterin, 5,10-dideazaaminopterin, and analogues on type II collagen-induced arthritis in mice.,  40  (3): [PMID:9022805] [10.1021/jm950553y]

2. Taylor EC, Harrington PJ, Fletcher SR, Beardsley GP, Moran RG..  (1985)  Synthesis of the antileukemic agents 5,10-dideazaaminopterin and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin.,  28  (7): [PMID:4009615] [10.1021/jm00145a012]

Source

Source(1):

• Scientific Literature