2-(((2R,3S,4R,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)ethylphosphonic acid

ID: ALA4790401

PubChem CID: 162669477

Max Phase: Preclinical

Molecular Formula: C19H23ClN5O7P

Molecular Weight: 499.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=P(O)(O)CCOC[C@H]1O[C@@H](n2cnc3c(NCc4ccccc4)nc(Cl)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H23ClN5O7P/c20-19-23-16(21-8-11-4-2-1-3-5-11)13-17(24-19)25(10-22-13)18-15(27)14(26)12(32-18)9-31-6-7-33(28,29)30/h1-5,10,12,14-15,18,26-27H,6-9H2,(H,21,23,24)(H2,28,29,30)/t12-,14-,15-,18-/m1/s1

Standard InChI Key:  AJRXCVVGNJCZJU-SCFUHWHPSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   21.2508   -4.6582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9605   -4.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9577   -3.4261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2490   -3.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5428   -4.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5440   -3.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7678   -3.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2868   -3.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7658   -4.5003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6688   -4.6562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.2453   -2.2036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9511   -1.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6607   -2.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6595   -3.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3682   -3.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0750   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0686   -2.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3593   -1.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5159   -5.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7384   -5.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7372   -6.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5141   -6.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9952   -5.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7655   -7.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8124   -5.9418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0754   -6.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3293   -6.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6675   -6.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9214   -6.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2596   -7.1185    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.5135   -6.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3438   -7.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0437   -6.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  2 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 19  9  1  1
 22 24  1  6
 23 25  1  6
 21 26  1  1
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790401

   ---

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: 499.85

Molecular Weight (Monoisotopic): 499.1024

AlogP: 0.91

#Rotatable Bonds: 9

Polar Surface Area: 172.08

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.77

CX Basic pKa: 2.18

CX LogP: -0.81

CX LogD: -2.46

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: 0.17

References

1. Sharif EU,Kalisiak J,Lawson KV,Miles DH,Newcomb E,Lindsey EA,Rosen BR,Debien LPP,Chen A,Zhao X,Young SW,Walker NP,Sträter N,Scaletti ER,Jin L,Xu G,Leleti MR,Powers JP.  (2021)  Discovery of Potent and Selective Methylenephosphonic Acid CD73 Inhibitors.,  64  (1.0): [PMID:33399453] [10.1021/acs.jmedchem.0c01835]

Source

Source(1):

• Scientific Literature