(S)-2-{5-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid

ID: ALA119248

PubChem CID: 135462415

Max Phase: Preclinical

Molecular Formula: C21H24N6O6

Molecular Weight: 456.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CNc1ccc3c(c1)CN([C@@H](CCC(=O)O)C(=O)O)C3=O)C2

Standard InChI:  InChI=1S/C21H24N6O6/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/h1-2,6,10,15,23H,3-5,7-9H2,(H,28,29)(H,32,33)(H4,22,24,25,26,30)/t10?,15-/m0/s1

Standard InChI Key:  SRMMXYVBSDDVLL-WRXSAAJRSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
    9.9000   -3.5917    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
    2.9167   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167   -2.9250    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
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    8.6292   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250   -3.5875    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
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    2.9167   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -2.3500    0.0000 O   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
    1.4792   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -6.0667    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
    7.2042   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -4.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4292   -2.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7292   -6.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5500   -3.5792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 13  1  0
  3  2  2  0
  4 15  1  0
  5  1  1  0
  6  7  1  0
  7  4  2  0
  8  3  1  0
  9  5  1  0
 10 11  1  0
 11  1  1  0
 12  1  1  0
 13 27  1  0
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 16  9  2  0
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 19 29  1  0
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 21 10  2  0
 22 14  2  0
 23 30  1  0
 24  8  1  0
 25 28  1  0
 26 19  2  0
 27 23  1  0
 28 21  1  0
 29 17  1  0
 30 25  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
  4  2  1  0
  6  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA119248

   ---

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: 456.46

Molecular Weight (Monoisotopic): 456.1757

AlogP: 0.73

#Rotatable Bonds: 8

Polar Surface Area: 191.00

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.30

CX Basic pKa: 4.00

CX LogP: -1.03

CX LogD: -6.16

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.06

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