2-{4-[2-(2,4-Diamino-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA173271

PubChem CID: 13912571

Max Phase: Preclinical

Molecular Formula: C21H26N6O5

Molecular Weight: 442.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)NCC(CCc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C21H26N6O5/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/h3-6,12,15H,1-2,7-10H2,(H,25,30)(H,28,29)(H,31,32)(H5,22,23,24,26,27)

Standard InChI Key:  JVKOZIXIYHORFY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
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   -1.8208   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -0.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8583   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -1.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500    0.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625    1.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9292    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167    1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375    1.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3750   -1.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792    1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417    0.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  6  2  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7 12  1  0
  8  2  1  0
  9  7  1  0
 10 11  1  0
 11  9  1  0
 12 21  1  0
 13  4  1  0
 14 24  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  1  0
 24 20  1  0
 25 10  1  0
 26 23  1  0
 27 31  1  0
 28 14  1  0
 29 27  2  0
 30 27  1  0
 31 32  1  0
 32 26  1  0
  4  5  2  0
 26 13  1  0
 22 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA173271

   2-{4-[2-(2,4-Diamino-5,6,7,8-tetrahydro-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: 442.48

Molecular Weight (Monoisotopic): 442.1965

AlogP: 0.91

#Rotatable Bonds: 9

Polar Surface Area: 193.55

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.57

CX Basic pKa: 7.86

CX LogP: -0.76

CX LogD: -4.40

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.31

References

1. 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