Isobutyric 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: ALA3228716

Chembl Id: CHEMBL3228716

PubChem CID: 90668616

Max Phase: Preclinical

Molecular Formula: C14H17N4O7PS

Molecular Weight: 416.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(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/C14H17N4O7PS/c1-6(2)14(19)24-10-9-7(3-22-26(20,21)25-9)23-13(10)18-5-17-8-11(18)15-4-16-12(8)27/h4-7,9-10,13H,3H2,1-2H3,(H,20,21)(H,15,16,27)/t7-,9-,10-,13-/m1/s1

Standard InChI Key:  SIKUYTPYFMPQMD-QYVSTXNMSA-N

Alternative Forms

1. Parent:

   

   ALA3228716

   [(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-methylpropanoate

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: 416.35

Molecular Weight (Monoisotopic): 416.0556

AlogP: 1.47

#Rotatable Bonds: 3

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: 0.40

CX LogD: -1.51

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 1.18

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