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

ID: ALA4166099

PubChem CID: 145954726

Max Phase: Preclinical

Molecular Formula: C17H22N6O7

Molecular Weight: 422.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H22N6O7/c18-17-22-14-9(15(28)23-17)6-8(20-14)7-12(25)19-5-1-2-11(24)21-10(16(29)30)3-4-13(26)27/h6,10H,1-5,7H2,(H,19,25)(H,21,24)(H,26,27)(H,29,30)(H4,18,20,22,23,28)/t10-/m0/s1

Standard InChI Key:  ZUPOLQOQXJAAHS-JTQLQIEISA-N

Molfile:  

     RDKit          2D

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   35.0558   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4683   -3.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4605   -1.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2777   -1.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0480   -0.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0636   -3.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4761   -4.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0715   -5.1727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2933   -4.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6495   -3.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   27.3589   -4.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3589   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0683   -3.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0728   -4.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8521   -4.4576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   28.8449   -3.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1523   -3.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5570   -3.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3783   -3.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1445   -2.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7871   -2.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3589   -2.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9424   -4.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6043   -2.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0103   -1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8275   -1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2335   -0.9310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11 12  1  0
 11 14  1  0
 12 13  2  0
 13 16  1  0
 15 14  1  0
 15 16  2  0
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 17 18  1  0
 18 19  2  0
 19 15  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 14 25  2  0
 12 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4166099

   ---

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: 422.40

Molecular Weight (Monoisotopic): 422.1550

AlogP: -1.29

#Rotatable Bonds: 11

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: 3.41

CX Basic pKa: 4.88

CX LogP: -3.29

CX LogD: -8.37

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.21

Np Likeness Score: -0.15

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