4-(Methylsulfanyl)-8-(beta-D-ribofuranosyl)-8H-thieno[2',3':4,5]-pyrrolo[2,3-d]pyrimidine-5'-O-monophosphate Sodium Salt

ID: ALA4084001

PubChem CID: 137646313

Max Phase: Preclinical

Molecular Formula: C14H15N3NaO7PS2

Molecular Weight: 433.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ncnc2c1c1sccc1n2[C@@H]1O[C@H](COP(=O)([O-])O)[C@@H](O)[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C14H16N3O7PS2.Na/c1-26-13-8-11-6(2-3-27-11)17(12(8)15-5-16-13)14-10(19)9(18)7(24-14)4-23-25(20,21)22;/h2-3,5,7,9-10,14,18-19H,4H2,1H3,(H2,20,21,22);/q;+1/p-1/t7-,9-,10-,14-;/m1./s1

Standard InChI Key:  XYDBUVLKGXAXGU-WPPLYIOHSA-M

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   26.6027   -2.8130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6027   -3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3125   -4.0494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0264   -3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0264   -2.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3098   -2.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3098   -1.5761    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.0194   -1.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8102   -2.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2990   -3.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8179   -3.8846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0782   -4.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6022   -5.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0888   -5.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8745   -5.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8745   -4.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5298   -4.4258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5441   -6.2201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8394   -6.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0358   -6.9605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7863   -7.7469    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.9785   -7.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3406   -8.3574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7863   -8.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0795   -2.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0795   -2.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2926   -1.8784    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.5095   -9.1500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  4  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  7  8  1  0
  9  5  1  0
  9 10  2  0
 11 10  1  0
  4 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 16 17  1  6
 15 18  1  6
 14 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 10 25  1  0
 25 26  2  0
 26 27  1  0
 27  9  1  0
M  CHG  2  24  -1  28   1
M  END

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: 433.40

Molecular Weight (Monoisotopic): 433.0167

AlogP: 1.10

#Rotatable Bonds: 5

Polar Surface Area: 147.16

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.22

CX Basic pKa: 5.13

CX LogP: -2.11

CX LogD: -2.57

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: 0.07

References

1. Tichý M, Smoleń S, Tloušt'ová E, Pohl R, Oždian T, Hejtmánková K, Lišková B, Gurská S, Džubák P, Hajdúch M, Hocek M..  (2017)  Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides.,  60  (6): [PMID:28221790] [10.1021/acs.jmedchem.6b01766]

Source

Source(1):

• Scientific Literature