(((2R,3S,4R,5R)-5-(2-chloro-6-((1-methyl-1H-pyrazol-4-yl)methylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)methylphosphonic acid

ID: ALA4782237

PubChem CID: 153325460

Max Phase: Preclinical

Molecular Formula: C16H21ClN7O7P

Molecular Weight: 489.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(CNc2nc(Cl)nc3c2ncn3[C@@H]2O[C@H](COCP(=O)(O)O)[C@@H](O)[C@H]2O)cn1

Standard InChI:  InChI=1S/C16H21ClN7O7P/c1-23-4-8(3-20-23)2-18-13-10-14(22-16(17)21-13)24(6-19-10)15-12(26)11(25)9(31-15)5-30-7-32(27,28)29/h3-4,6,9,11-12,15,25-26H,2,5,7H2,1H3,(H,18,21,22)(H2,27,28,29)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  QFNKMQZMYFPSSK-SDBHATRESA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    8.3532  -11.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0629  -10.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0601  -10.0916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3514   -9.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6452  -10.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6464  -10.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8702   -9.8447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892  -10.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8682  -11.1658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7712  -11.3217    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3477   -8.8691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0535   -8.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7631   -8.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6183  -11.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408  -12.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396  -13.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6165  -13.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0977  -12.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8679  -14.0441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149  -12.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778  -13.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317  -13.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699  -13.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541  -14.4510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.1923  -14.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6002  -14.7845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688  -13.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8536   -9.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6537   -9.8385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0590   -9.1289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5094   -8.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9895  -10.5835    0.0000 C   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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 14  9  1  1
 17 19  1  6
 18 20  1  6
 16 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  1  0
 13 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 13  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782237

   ---

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: 489.81

Molecular Weight (Monoisotopic): 489.0929

AlogP: -0.40

#Rotatable Bonds: 8

Polar Surface Area: 189.90

Molecular Species: ACID

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.35

CX Basic pKa: 2.31

CX LogP: -2.65

CX LogD: -3.85

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.20

Np Likeness Score: -0.26

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