(S)-2-{5-[(2-Amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid

ID: ALA115851

PubChem CID: 135415174

Max Phase: Preclinical

Molecular Formula: C21H20N6O6

Molecular Weight: 452.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2cc(CNc3ccc4c(c3)CN([C@@H](CCC(=O)O)C(=O)O)C4=O)cnc2n1

Standard InChI:  InChI=1S/C21H20N6O6/c22-21-25-17-14(18(30)26-21)5-10(8-24-17)7-23-12-1-2-13-11(6-12)9-27(19(13)31)15(20(32)33)3-4-16(28)29/h1-2,5-6,8,15,23H,3-4,7,9H2,(H,28,29)(H,32,33)(H3,22,24,25,26,30)/t15-/m0/s1

Standard InChI Key:  IBEWQERHBNNAHP-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
    9.9125   -3.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -4.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6292   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7375   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7292   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9292   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917   -2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -4.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3167   -6.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0292   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4417   -2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -6.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5625   -3.5750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3  1  1  0
  4  6  1  0
  5 13  1  0
  6  7  2  0
  7 15  1  0
  8  2  1  0
  9  3  1  0
 10 11  1  0
 11  1  1  0
 12  1  1  0
 13 27  2  0
 14 12  1  0
 15 22  2  0
 16  9  2  0
 17 12  1  0
 18  3  2  0
 19 29  1  0
 20  6  1  0
 21 10  2  0
 22 30  1  0
 23 14  2  0
 24 28  1  0
 25  8  1  0
 26 19  2  0
 27 22  1  0
 28 21  1  0
 29 17  1  0
 30 24  1  0
 31 16  1  0
 32 14  1  0
 33 19  1  0
 12 34  1  1
  9 10  1  0
 31 28  2  0
  7  5  1  0
  4  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA115851

   ---

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: 452.43

Molecular Weight (Monoisotopic): 452.1444

AlogP: 1.20

#Rotatable Bonds: 8

Polar Surface Area: 191.86

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.27

CX Basic pKa: 2.38

CX LogP: 0.11

CX LogD: -5.98

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -0.43

References

1. Rosowsky A, Forsch RA, Null A, Moran RG..  (1999)  5-deazafolate analogues with a rotationally restricted glutamate or ornithine side chain: synthesis and binding interaction with folylpolyglutamate synthetase.,  42  (18): [PMID:10479284] [10.1021/jm9807205]

Source

Source(1):

• Scientific Literature