Dodecanoic 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: ALA3228719

Chembl Id: CHEMBL3228719

PubChem CID: 90668619

Max Phase: Preclinical

Molecular Formula: C22H33N4O7PS

Molecular Weight: 528.57

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H33N4O7PS/c1-2-3-4-5-6-7-8-9-10-11-16(27)32-19-18-15(12-30-34(28,29)33-18)31-22(19)26-14-25-17-20(26)23-13-24-21(17)35/h13-15,18-19,22H,2-12H2,1H3,(H,28,29)(H,23,24,35)/t15-,18-,19-,22-/m1/s1

Standard InChI Key:  IHEJMBVENLTMHH-CIVUBGFFSA-N

Alternative Forms

1. Parent:

   

   ALA3228719

   [(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] dodecanoate

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: 528.57

Molecular Weight (Monoisotopic): 528.1808

AlogP: 4.73

#Rotatable Bonds: 12

Polar Surface Area: 137.79

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.95

CX Basic pKa: 1.21

CX LogP: 3.86

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.17

Np Likeness Score: 0.91

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