[[(2R,3R,4S,5R)-5-[2-Chloro-6-(ethylamino)purin-9-yl]-4-fluoro-3-hydroxyoxolan-2-yl]methoxyhydroxyphosphoryl]-methylphosphonic Acid

ID: ALA4755896

PubChem CID: 130424059

Max Phase: Preclinical

Molecular Formula: C13H19ClFN5O8P2

Molecular Weight: 489.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@@H]1F

Standard InChI:  InChI=1S/C13H19ClFN5O8P2/c1-2-16-10-8-11(19-13(14)18-10)20(4-17-8)12-7(15)9(21)6(28-12)3-27-30(25,26)5-29(22,23)24/h4,6-7,9,12,21H,2-3,5H2,1H3,(H,25,26)(H,16,18,19)(H2,22,23,24)/t6-,7+,9-,12-/m1/s1

Standard InChI Key:  GKJSHSNXECPIRO-MCOZSMFQSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   15.6202  -10.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2104  -10.2796    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.7918  -10.9963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1774  -10.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7675  -10.2629    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3489  -10.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3218   -8.0395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0697   -8.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0487   -7.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8226   -7.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5199   -9.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2617   -9.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0501   -6.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7790   -8.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3326   -6.6251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0322  -10.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3015   -9.7189    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.2535   -9.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7567   -6.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5283   -7.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5109  -10.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5991  -10.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5268   -6.9097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7500   -5.6473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9298   -9.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4933   -9.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0508   -9.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0296   -5.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0228   -4.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2426   -8.2059    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  8  7  1  1
  7  9  1  0
  7 10  1  0
 11  8  1  0
  8 12  1  0
  9 13  2  0
  9 14  1  0
 10 15  2  0
 11 16  1  0
 11 17  1  1
 12 18  1  0
 13 19  1  0
 14 20  2  0
 16 21  1  6
 18 22  1  1
 19 23  2  0
 19 24  1  0
 22 25  1  0
 13 15  1  0
 16 18  1  0
 20 23  1  0
 25  2  1  0
  2 26  1  0
 26  5  1  0
  5 27  2  0
 24 28  1  0
 28 29  1  0
 20 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755896

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 489.72

Molecular Weight (Monoisotopic): 489.0381

AlogP: 0.85

#Rotatable Bonds: 8

Polar Surface Area: 189.15

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.94

CX Basic pKa: 2.19

CX LogP: -2.38

CX LogD: -5.70

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 0.23

References

1. Lawson KV,Kalisiak J,Lindsey EA,Newcomb ET,Leleti MR,Debien L,Rosen BR,Miles DH,Sharif EU,Jeffrey JL,Tan JBL,Chen A,Zhao S,Xu G,Fu L,Jin L,Park TW,Berry W,Moschütz S,Scaletti E,Sträter N,Walker NP,Young SW,Walters MJ,Schindler U,Powers JP.  (2020)  Discovery of AB680: A Potent and Selective Inhibitor of CD73.,  63  (20.0): [PMID:32614585] [10.1021/acs.jmedchem.0c00525]

Source

Source(1):

• Scientific Literature