2,2-Dimethyl-propionic acid(4aR,6R,7R,7aR)-2-hydroxy-2-oxo-6-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-2lambda*5*-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl ester

ID: ALA3228717

Chembl Id: CHEMBL3228717

PubChem CID: 90668617

Max Phase: Preclinical

Molecular Formula: C15H19N4O7PS

Molecular Weight: 430.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c(=S)[nH]cnc21

Standard InChI:  InChI=1S/C15H19N4O7PS/c1-15(2,3)14(20)25-10-9-7(4-23-27(21,22)26-9)24-13(10)19-6-18-8-11(19)16-5-17-12(8)28/h5-7,9-10,13H,4H2,1-3H3,(H,21,22)(H,16,17,28)/t7-,9-,10-,13-/m1/s1

Standard InChI Key:  KBKPBRWMLZMPAB-QYVSTXNMSA-N

Alternative Forms

1. Parent:

   

   ALA3228717

   [(4aR,6R,7R,7aR)-2-hydroxy-2-oxo-6-(6-sulfanylidene-3H-purin-9-yl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] 2,2-dimethylpropanoate

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: 430.38

Molecular Weight (Monoisotopic): 430.0712

AlogP: 1.86

#Rotatable Bonds: 2

Polar Surface Area: 137.79

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.95

CX Basic pKa: 1.21

CX LogP: 0.96

CX LogD: -0.95

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: 0.93

References

1. Meyer RB, Stone TE, Ullman B..  (1979)  2'-O-Acyl-6-thioinosine cyclic 3',5'-phosphates as prodrugs of thioinosinic acid.,  22  (7): [PMID:221658] [10.1021/jm00193a012]

Source

Source(1):

• Scientific Literature