N-(Purin-6-yl)-glycyl-(S)-glutamic acid hydrate

ID: ALA3806212

PubChem CID: 127052621

Max Phase: Preclinical

Molecular Formula: C12H16N6O6

Molecular Weight: 322.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H14N6O5.H2O/c19-7(18-6(12(22)23)1-2-8(20)21)3-13-10-9-11(15-4-14-9)17-5-16-10;/h4-6H,1-3H2,(H,18,19)(H,20,21)(H,22,23)(H2,13,14,15,16,17);1H2/t6-;/m0./s1

Standard InChI Key:  SKDLYOGKWNHHEO-RGMNGODLSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.0889    5.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -1.2394    7.6730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739    9.4755    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
   -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
   -7.2072    9.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1610   11.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  9  2  0
  8  5  2  0
  5  2  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  1  1
 16 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
M  END

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: 322.28

Molecular Weight (Monoisotopic): 322.1026

AlogP: -0.80

#Rotatable Bonds: 8

Polar Surface Area: 170.19

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.12

CX Basic pKa: 5.03

CX LogP: -3.00

CX LogD: -8.25

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.42

Np Likeness Score: -0.41

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