(S)-2-{5-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)-acetylamino]-pentanoylamino}-pentanedioic acid

ID: ALA4174018

PubChem CID: 145949332

Max Phase: Preclinical

Molecular Formula: C18H24N6O7

Molecular Weight: 436.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H24N6O7/c19-18-23-15-10(16(29)24-18)7-9(21-15)8-13(26)20-6-2-1-3-12(25)22-11(17(30)31)4-5-14(27)28/h7,11H,1-6,8H2,(H,20,26)(H,22,25)(H,27,28)(H,30,31)(H4,19,21,23,24,29)/t11-/m0/s1

Standard InChI Key:  KYKDIKFUXRYZEH-NSHDSACASA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   38.3626   -4.5606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3626   -5.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0720   -5.7905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0720   -4.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7814   -4.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7859   -5.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5652   -5.6297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0441   -4.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5580   -4.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8654   -4.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2700   -4.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0913   -4.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8575   -3.5365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.5001   -3.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0720   -3.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6555   -5.7957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3173   -3.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7233   -2.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5405   -2.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9465   -2.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7637   -2.1001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.5354   -1.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   47.1697   -1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9869   -1.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7585   -0.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.1646    0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.9414   -0.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   48.3981   -2.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.2153   -2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.6265   -2.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   49.6213   -1.3820    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
 19 20  1  0
 20 21  1  0
 20 22  2  0
 23 21  1  6
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174018

   ---

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: 436.43

Molecular Weight (Monoisotopic): 436.1706

AlogP: -0.90

#Rotatable Bonds: 12

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: 3.58

CX Basic pKa: 4.90

CX LogP: -2.80

CX LogD: -7.85

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.20

Np Likeness Score: -0.09

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