{[(2R,3R,4S)-5-(2-Amino-6-oxo-1,6-dihydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid

ID: ALA1164951

Chembl Id: CHEMBL1164951

PubChem CID: 135406506

Max Phase: Preclinical

Molecular Formula: C11H17N5O10P2

Molecular Weight: 441.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C11H17N5O10P2/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(26-10)1-25-28(23,24)3-27(20,21)22/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H2,20,21,22)(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  OCJWYBKRHNXUME-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA1164951

   PHOSPHOMETHYLPHOSPHONIC ACID GUANOSYL ESTER

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

Calculated Properties

Molecular Weight: 441.23

Molecular Weight (Monoisotopic): 441.0451

AlogP: -2.34

#Rotatable Bonds: 6

Polar Surface Area: 243.34

Molecular Species: ACID

HBA: 11

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.98

CX Basic pKa: 0.33

CX LogP: -4.74

CX LogD: -8.97

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.23

Np Likeness Score: 0.95

References

1. Vincent SP, Grenier S, Mioskowski C, Salesse C, Lebeau L..  (2001)  Probing the transducin nucleotide binding site with GDP analogues.,  11  (9): [PMID:11354373] [10.1016/s0960-894x(01)00172-x]

2. Wexselblatt E, Katzhendler J, Saleem-Batcha R, Hansen G, Hilgenfeld R, Glaser G, Vidavski RR..  (2010)  ppGpp analogues inhibit synthetase activity of Rel proteins from Gram-negative and Gram-positive bacteria.,  18  (12): [PMID:20483622] [10.1016/j.bmc.2010.04.064]

3. Bhattarai S, Pippel J, Scaletti E, Idris R, Freundlieb M, Rolshoven G, Renn C, Lee SY, Abdelrahman A, Zimmermann H, El-Tayeb A, Müller CE, Sträter N..  (2020)  2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5'-nucleotidase (CD73) Inhibitors with Variable Binding Modes.,  63  (6): [PMID:32045236] [10.1021/acs.jmedchem.9b01611]

Source

Source(1):

• Scientific Literature