Dimethyl N-(purin-6-yl)-glycyl-(S)-glutamate

ID: ALA3806314

PubChem CID: 127052616

Max Phase: Preclinical

Molecular Formula: C14H18N6O5

Molecular Weight: 350.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC[C@H](NC(=O)CNc1ncnc2[nH]cnc12)C(=O)OC

Standard InChI:  InChI=1S/C14H18N6O5/c1-24-10(22)4-3-8(14(23)25-2)20-9(21)5-15-12-11-13(17-6-16-11)19-7-18-12/h6-8H,3-5H2,1-2H3,(H,20,21)(H2,15,16,17,18,19)/t8-/m0/s1

Standard InChI Key:  NNEKLSKBNFBVKF-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971    3.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    5.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    6.0270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461    5.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5785    7.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2772    8.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731    9.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394    7.6730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749    8.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2326   10.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    9.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1655   10.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598   12.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1964   12.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2072    9.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  6 12  1  0
 12 13  1  0
 12 14  2  0
 15 13  1  1
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  1  0
 17 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3806314

   ---

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: 350.34

Molecular Weight (Monoisotopic): 350.1339

AlogP: -0.62

#Rotatable Bonds: 8

Polar Surface Area: 148.19

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.86

CX Basic pKa: 4.98

CX LogP: -1.35

CX LogD: -1.35

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -0.55

References

1. Krasnov VP, Vigorov AY, Musiyak VV, Nizova IA, Gruzdev DA, Matveeva TV, Levit GL, Kravchenko MA, Skornyakov SN, Bekker OB, Danilenko VN, Charushin VN..  (2016)  Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides.,  26  (11): [PMID:27107949] [10.1016/j.bmcl.2016.04.017]

Source

Source(1):

• Scientific Literature