2-Hydroxymethyl-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3,4-diol

ID: ALA388931

Cas Number: 342-69-8

PubChem CID: 9570

Product Number: M133388, Order Now?

Max Phase: Preclinical

Molecular Formula: C11H14N4O4S

Molecular Weight: 298.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  ZDRFDHHANOYUTE-IOSLPCCCSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -2.0155   -2.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4343   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4343   -0.7041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6497   -0.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948    0.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948    1.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898    1.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    1.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    2.6529    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898    3.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    1.4154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898    0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648   -1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -1.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6497   -1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  3  4  1  0
 19  3  1  0
  5  4  1  0
  5  6  1  1
  5 17  1  0
  7  6  1  0
 16  6  1  0
  7  8  2  0
  9  8  1  0
  9 10  2  0
 16  9  1  0
 10 11  1  0
 10 13  1  0
 12 11  1  0
 14 13  2  0
 14 15  1  0
 16 15  2  0
 17 18  1  6
 17 19  1  0
 19 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA388931

   6-Methylmercaptopurine riboside

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: 298.32

Molecular Weight (Monoisotopic): 298.0736

AlogP: -0.84

#Rotatable Bonds: 3

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.31

CX LogP: -0.63

CX LogD: -0.63

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.50

Np Likeness Score: 0.75

References

1. Goebel RJ, Adams AD, McKernan PA, Murray BK, Robins RK, Revankar GR, Canonico PG..  (1982)  Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.,  25  (11): [PMID:7143371] [10.1021/jm00353a012]

2. Shealy YF, O'Dell CA, Shannon WM, Arnett G..  (1984)  Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.,  27  (11): [PMID:6092635] [10.1021/jm00377a007]

3. Lin TS, Cheng JC, Ishiguro K, Sartorelli AC..  (1985)  Purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives as potential inducers of the differentiation of the Friend erythroleukemia.,  28  (10): [PMID:3862866] [10.1021/jm00148a018]

4. Lombardo F, Shalaeva MY, Tupper KA, Gao F..  (2001)  ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.,  44  (15): [PMID:11448232] [10.1021/jm0100990]

5. Lombardo F, Shalaeva MY, Tupper KA, Gao F, Abraham MH..  (2000)  ElogPoct: a tool for lipophilicity determination in drug discovery.,  43  (15): [PMID:10956200] [10.1021/jm0000822]

6. Krenitsky TA, Rideout JL, Koszalka GW, Inmon RB, Chao EY, Elion GB, Latter VS, Williams RB..  (1982)  Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 1. Synthesis and activity of some nucleosides of purines and 4-(alkylthio)pyrazolo[3,4-d]pyrimidines.,  25  (1): [PMID:7086819] [10.1021/jm00343a007]

7. Ghose AK, Crippen GM, Revankar GR, McKernan PA, Smee DF, Robins RK..  (1989)  Analysis of the in vitro antiviral activity of certain ribonucleosides against parainfluenza virus using a novel computer aided receptor modeling procedure.,  32  (4): [PMID:2539476] [10.1021/jm00124a005]

8. Ikejiri M, Saijo M, Morikawa S, Fukushi S, Mizutani T, Kurane I, Maruyama T..  (2007)  Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents.,  17  (9): [PMID:17336519] [10.1016/j.bmcl.2007.02.026]

9. Akoachere M, Squires RC, Nour AM, Angelov L, Brojatsch J, Abel-Santos E..  (2007)  Identification of an in vivo inhibitor of Bacillus anthracis spore germination.,  282  (16): [PMID:17296608] [10.1074/jbc.m611432200]

10. Zhu Z, Buolamwini JK..  (2008)  Constrained NBMPR analogue synthesis, pharmacophore mapping and 3D-QSAR modeling of equilibrative nucleoside transporter 1 (ENT1) inhibitory activity.,  16  (7): [PMID:18289860] [10.1016/j.bmc.2008.01.044]

11. Ducati RG, Basso LA, Santos DS, de Azevedo WF..  (2010)  Crystallographic and docking studies of purine nucleoside phosphorylase from Mycobacterium tuberculosis.,  18  (13): [PMID:20570524] [10.1016/j.bmc.2010.05.009]

12. Alvarez Z, Lee K, Abel-Santos E..  (2010)  Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.,  54  (12): [PMID:20921305] [10.1128/aac.01029-10]

13. Abreu LS, do Nascimento YM, Costa RDS, Guedes MLS, Souza BNRF, Pena LJ, Costa VCO, Scotti MT, Braz-Filho R, Barbosa-Filho JM, da Silva MS, Velozo EDS, Tavares JF..  (2019)  Tri- and Diterpenoids from Stillingia loranthacea as Inhibitors of Zika Virus Replication.,  82  (10): [PMID:31599155] [10.1021/acs.jnatprod.9b00251]

14. Crespo RA, Dang Q, Zhou NE, Guthrie LM, Snavely TC, Dong W, Loesch KA, Suzuki T, You L, Wang W, O'Malley T, Parish T, Olsen DB, Sacchettini JC..  (2019)  Structure-Guided Drug Design of 6-Substituted Adenosine Analogues as Potent Inhibitors of Mycobacterium tuberculosis Adenosine Kinase.,  62  (9): [PMID:31002508] [10.1021/acs.jmedchem.9b00020]

Source

Source(1):

• Scientific Literature