5'-methylthiocoformycin

ID: ALA1234234

PubChem CID: 16720828

Max Phase: Preclinical

Molecular Formula: C12H18N4O4S

Molecular Weight: 314.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC[C@H]1O[C@@H](n2cnc3c2N=CNC[C@H]3O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H18N4O4S/c1-21-3-7-9(18)10(19)12(20-7)16-5-15-8-6(17)2-13-4-14-11(8)16/h4-7,9-10,12,17-19H,2-3H2,1H3,(H,13,14)/t6-,7-,9-,10-,12-/m1/s1

Standard InChI Key:  QLPPCUVJNCMYFD-SANHVUMCSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.8229   -2.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -2.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8108   -1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -1.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8108   -0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -0.2730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -1.8673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081   -1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -0.5325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1932    0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.9196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    0.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    1.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    2.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1301    1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    2.6375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113    3.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  2  8  1  0
  3  4  1  0
  5  4  1  0
  5  6  2  0
  7  6  1  0
  7  8  2  0
  7 11  1  0
  8  9  1  0
 10  9  2  0
 10 11  1  0
 12 11  1  6
 12 15  1  0
 12 13  1  0
 13 17  1  0
 13 14  1  1
 16 15  1  0
 16 19  1  6
 17 16  1  0
 17 18  1  1
 19 20  1  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1234234

   (8r)-3-(5-S-Methyl-5-Thio-Beta-D-Ribofuranosyl)-3,6,7,8-Tetrahydroimidazo[4,5-D][1,3]diazepin-8-Ol

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: 314.37

Molecular Weight (Monoisotopic): 314.1049

AlogP: -0.84

#Rotatable Bonds: 3

Polar Surface Area: 112.13

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.39

CX Basic pKa: 8.21

CX LogP: -1.43

CX LogD: -2.26

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 0.68

References

1. Cheviet T, Lefebvre-Tournier I, Wein S, Peyrottes S..  (2019)  Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.,  62  (18): [PMID:30964283] [10.1021/acs.jmedchem.9b00182]

Source

Source(1):

• Scientific Literature