N-(Purin-6-yl)-glycyl-(S)-phenylalanine hydrate

ID: ALA3805255

PubChem CID: 127052618

Max Phase: Preclinical

Molecular Formula: C16H18N6O4

Molecular Weight: 340.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O.O=C(CNc1ncnc2[nH]cnc12)N[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C16H16N6O3.H2O/c23-12(7-17-14-13-15(19-8-18-13)21-9-20-14)22-11(16(24)25)6-10-4-2-1-3-5-10;/h1-5,8-9,11H,6-7H2,(H,22,23)(H,24,25)(H2,17,18,19,20,21);1H2/t11-;/m0./s1

Standard InChI Key:  FWUYOOKTUORPNT-MERQFXBCSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.0889    5.6358    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
   -6.1638   10.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1550   12.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8516   12.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569   12.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5657   10.5272    0.0000 C   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  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  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: 340.34

Molecular Weight (Monoisotopic): 340.1284

AlogP: 0.58

#Rotatable Bonds: 7

Polar Surface Area: 132.89

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.50

CX Basic pKa: 5.00

CX LogP: -0.52

CX LogD: -3.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -0.66

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