(S)-2-(4-((2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)methyl)benzamido)pentanedioic acid

ID: ALA498800

PubChem CID: 136045806

Max Phase: Preclinical

Molecular Formula: C19H19N5O6

Molecular Weight: 413.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(Cc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C19H19N5O6/c20-19-23-15-12(17(28)24-19)8-11(21-15)7-9-1-3-10(4-2-9)16(27)22-13(18(29)30)5-6-14(25)26/h1-4,8,13H,5-7H2,(H,22,27)(H,25,26)(H,29,30)(H4,20,21,23,24,28)/t13-/m0/s1

Standard InChI Key:  LHMUZCZEUVKRGD-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.7851    1.0713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    0.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.3529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609    1.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -0.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -0.9148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930   -0.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5735    1.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    0.3089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8630   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594   -0.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579   -0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    0.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    0.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033    0.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    0.4346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8934    1.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3545    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0851    0.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223    1.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207    2.1390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    2.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8799   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5420   -0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 14 15  1  0
  3  6  1  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
 16 19  1  0
  9  5  1  0
 19 20  1  0
  5  4  1  0
 19 21  2  0
  4 10  2  0
 20 22  1  0
  5  6  2  0
 22 23  1  0
  2 11  1  0
 22 24  1  6
 24 25  2  0
  8 12  1  0
 24 26  1  0
  1  2  1  0
 23 27  1  0
 12 13  1  0
 27 28  1  0
  1  4  1  0
 28 29  2  0
 13 14  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA498800

   ---

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: 413.39

Molecular Weight (Monoisotopic): 413.1335

AlogP: 0.47

#Rotatable Bonds: 8

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.36

CX Basic pKa: 3.09

CX LogP: -0.39

CX LogD: -6.23

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -0.01

References

1. Deng Y, Wang Y, Cherian C, Hou Z, Buck SA, Matherly LH, Gangjee A..  (2008)  Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity.,  51  (16): [PMID:18680275] [10.1021/jm8003366]

Source

Source(1):

• Scientific Literature