[[(2R,3S,4R,5R)-5-[4-(Benzylamino)-6-chloropyrazolo[3,4-d]-pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxyhydroxyphosphoryl]methylphosphonic Acid

ID: ALA4790144

PubChem CID: 130205976

Max Phase: Preclinical

Molecular Formula: C18H22ClN5O9P2

Molecular Weight: 549.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=P(O)(O)CP(=O)(O)OC[C@H]1O[C@@H](n2ncc3c(NCc4ccccc4)nc(Cl)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H22ClN5O9P2/c19-18-22-15(20-6-10-4-2-1-3-5-10)11-7-21-24(16(11)23-18)17-14(26)13(25)12(33-17)8-32-35(30,31)9-34(27,28)29/h1-5,7,12-14,17,25-26H,6,8-9H2,(H,30,31)(H,20,22,23)(H2,27,28,29)/t12-,13-,14-,17-/m1/s1

Standard InChI Key:  WSMAWKQTHDXPAT-VMUDFCTBSA-N

Molfile:  

 
     RDKit          2D

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    8.7309   -8.7669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6192   -7.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6275   -6.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1884   -5.1215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9950   -8.7878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6232   -6.0239    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.1134   -3.4550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8212   -3.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6483   -8.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9493   -4.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9372   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4790144

   ---

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: 549.80

Molecular Weight (Monoisotopic): 549.0581

AlogP: 1.05

#Rotatable Bonds: 9

Polar Surface Area: 209.38

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.98

CX Basic pKa: 0.82

CX LogP: -1.42

CX LogD: -5.29

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.16

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