(S)-2-{3-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)-acetylamino]-propionylamino}-pentanedioic acid

ID: ALA4163732

PubChem CID: 145959529

Max Phase: Preclinical

Molecular Formula: C16H20N6O7

Molecular Weight: 408.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20N6O7/c17-16-21-13-8(14(27)22-16)5-7(19-13)6-11(24)18-4-3-10(23)20-9(15(28)29)1-2-12(25)26/h5,9H,1-4,6H2,(H,18,24)(H,20,23)(H,25,26)(H,28,29)(H4,17,19,21,22,27)/t9-/m0/s1

Standard InChI Key:  IPVCAFLQSKTPOY-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   13.2443   -3.3100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2443   -4.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537   -4.5358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537   -2.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6631   -3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6676   -4.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4469   -4.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9257   -3.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4397   -3.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7470   -3.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1517   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9730   -2.9869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7392   -2.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3818   -2.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537   -2.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5372   -4.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2031   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6156   -2.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4369   -2.9733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2110   -3.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8457   -2.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6671   -2.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4291   -1.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8379   -0.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6078   -1.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0796   -2.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9009   -2.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3175   -3.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3097   -2.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
  4 15  2  0
  2 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 21 19  1  6
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4163732

   ---

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: 408.37

Molecular Weight (Monoisotopic): 408.1393

AlogP: -1.68

#Rotatable Bonds: 10

Polar Surface Area: 220.36

Molecular Species: ACID

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.45

CX Basic pKa: 4.88

CX LogP: -3.58

CX LogD: -8.64

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: -0.22

References

1. Xing R, Zhang H, Yuan J, Zhang K, Li L, Guo H, Zhao L, Zhang C, Li S, Gao T, Liu Y, Wang L..  (2017)  Novel 6-substituted benzoyl and non-benzoyl straight chain pyrrolo[2,3-d]pyrimidines as potential antitumor agents with multitargeted inhibition of TS, GARFTase and AICARFTase.,  139  [PMID:28830032] [10.1016/j.ejmech.2017.08.032]

Source

Source(1):

• Scientific Literature