Methyl N-(purin-6-yl)-glycyl-(S)-valinate

ID: ALA3806017

PubChem CID: 127049211

Max Phase: Preclinical

Molecular Formula: C13H18N6O3

Molecular Weight: 306.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H18N6O3/c1-7(2)9(13(21)22-3)19-8(20)4-14-11-10-12(16-5-15-10)18-6-17-11/h5-7,9H,4H2,1-3H3,(H,19,20)(H2,14,15,16,17,18)/t9-/m0/s1

Standard InChI Key:  PXTBBXFLZJWRJG-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 22 23  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
   -4.8749    8.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    9.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166    7.6883    0.0000 O   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
   -5.9057   10.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739    9.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394    7.6730    0.0000 C   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  6
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  1  0
 17 20  1  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3806017

   ---

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: 306.33

Molecular Weight (Monoisotopic): 306.1440

AlogP: 0.08

#Rotatable Bonds: 6

Polar Surface Area: 121.89

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: 3.99

CX LogP: -0.25

CX LogD: -0.26

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: -0.85

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