2-{4-[(2-Amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-4-(ethoxy-hydroxy-phosphoryl)-butyric acid

ID: ALA294973

PubChem CID: 136046154

Max Phase: Preclinical

Molecular Formula: C21H25N6O7P

Molecular Weight: 504.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(O)CCC(NC(=O)c1ccc(NCc2cnc3nc(N)nc(O)c3c2)cc1)C(=O)O

Standard InChI:  InChI=1S/C21H25N6O7P/c1-2-34-35(32,33)8-7-16(20(30)31)25-18(28)13-3-5-14(6-4-13)23-10-12-9-15-17(24-11-12)26-21(22)27-19(15)29/h3-6,9,11,16,23H,2,7-8,10H2,1H3,(H,25,28)(H,30,31)(H,32,33)(H3,22,24,26,27,29)

Standard InChI Key:  FBRKPFQSNPGVGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    0.7000   -2.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -1.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -0.4792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -1.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2542   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167    0.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -2.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917    0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750    0.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  2  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7 20  1  0
  8 14  1  0
  9  3  1  0
 10  8  1  0
 11 12  1  0
 12 10  1  0
 13  5  1  0
 14 27  2  0
 15  4  1  0
 16 12  1  0
 17  7  2  0
 18  8  2  0
 19 24  1  0
 20 16  1  0
 21 11  2  0
 22  6  1  0
 23 30  1  0
 24  9  2  0
 25  7  1  0
 26 32  2  0
 27 33  1  0
 28  7  1  0
 29 23  1  0
 30 19  1  0
 31 11  1  0
 32 29  1  0
 33 29  2  0
 34 28  1  0
 35 34  1  0
  4  5  2  0
 13 19  2  0
 26 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA294973

   ---

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: 504.44

Molecular Weight (Monoisotopic): 504.1522

AlogP: 1.72

#Rotatable Bonds: 11

Polar Surface Area: 209.88

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.86

CX Basic pKa: 2.74

CX LogP: -0.66

CX LogD: -5.27

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: -0.48

References

1. Rosowsky A, Forsch RA, Reich VE, Freisheim JH, Moran RG..  (1992)  Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation.,  35  (9): [PMID:1578484] [10.1021/jm00087a012]

Source

Source(1):

• Scientific Literature