Hexanoic 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: ALA3228718

Chembl Id: CHEMBL3228718

PubChem CID: 90668618

Max Phase: Preclinical

Molecular Formula: C16H21N4O7PS

Molecular Weight: 444.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21N4O7PS/c1-2-3-4-5-10(21)26-13-12-9(6-24-28(22,23)27-12)25-16(13)20-8-19-11-14(20)17-7-18-15(11)29/h7-9,12-13,16H,2-6H2,1H3,(H,22,23)(H,17,18,29)/t9-,12-,13-,16-/m1/s1

Standard InChI Key:  HIOKVZCPBYALIJ-RVXWVPLUSA-N

Alternative Forms

1. Parent:

   

   ALA3228718

   [(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] hexanoate

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: 444.41

Molecular Weight (Monoisotopic): 444.0869

AlogP: 2.39

#Rotatable Bonds: 6

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: 1.19

CX LogD: -0.72

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: 1.06

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