ID: ALA4287314

Max Phase: Preclinical

Molecular Formula: C11H15ClFN5O8P2

Molecular Weight: 461.67

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@@H]1F

Standard InChI:  InChI=1S/C11H15ClFN5O8P2/c12-11-16-8(14)6-9(17-11)18(2-15-6)10-5(13)7(19)4(26-10)1-25-28(23,24)3-27(20,21)22/h2,4-5,7,10,19H,1,3H2,(H,23,24)(H2,14,16,17)(H2,20,21,22)/t4-,5+,7-,10-/m1/s1

Standard InChI Key:  VPXFTBZVQMXNLH-GQTRHBFLSA-N

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

Properties

Molecular Weight: 461.67

Molecular Weight (Monoisotopic): 461.0068

AlogP: 0.00

#Rotatable Bonds: 6

Polar Surface Area: 203.14

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.95

CX Basic pKa: 2.32

CX LogP: -3.20

CX LogD: -6.39

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: 0.50

References

1. Dumontet C, Peyrottes S, Rabeson C, Cros-Perrial E, Géant PY, Chaloin L, Jordheim LP..  (2018)  CD73 inhibition by purine cytotoxic nucleoside analogue-based diphosphonates.,  157  [PMID:30176535] [10.1016/j.ejmech.2018.08.035]

2. 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