2'-O-butyryl-6-thioinosine cyclic 3',5'-phosphate

ID: ALA3228715

Chembl Id: CHEMBL3228715

PubChem CID: 90668615

Max Phase: Preclinical

Molecular Formula: C14H17N4O7PS

Molecular Weight: 416.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI Key:  RYVLTQINLJXUEM-FRJWGUMJSA-N

Alternative Forms

1. Parent:

   

   ALA3228715

   [(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] butanoate

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: 1.61

#Rotatable Bonds: 4

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: 0.30

CX LogD: -1.61

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 1.09

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