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

ID: ALA4100457

PubChem CID: 137660280

Max Phase: Preclinical

Molecular Formula: C14H15N3O4S2

Molecular Weight: 353.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ncnc2c1c1ccsc1n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H15N3O4S2/c1-22-12-8-6-2-3-23-14(6)17(11(8)15-5-16-12)13-10(20)9(19)7(4-18)21-13/h2-3,5,7,9-10,13,18-20H,4H2,1H3/t7-,9-,10-,13-/m1/s1

Standard InChI Key:  VVTCIGWZJANTDX-QYVSTXNMSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   19.2437  -15.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2437  -16.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9536  -16.9308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6677  -16.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6677  -15.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9509  -15.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9509  -14.4530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.6648  -14.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4516  -15.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9404  -16.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4593  -16.7660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7196  -17.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2436  -18.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7302  -18.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5161  -18.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5161  -17.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1714  -17.3072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1858  -19.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4808  -19.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -19.8423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7252  -15.8355    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.7252  -15.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9341  -14.7596    0.0000 C   0  0  0  0  0  0  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
 10 21  1  0
 21 22  1  0
 22 23  2  0
 23  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100457

   ---

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: 353.43

Molecular Weight (Monoisotopic): 353.0504

AlogP: 0.98

#Rotatable Bonds: 3

Polar Surface Area: 100.63

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.22

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: -0.02

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