9-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purine-6-thione

ID: ALA448290

Chembl Id: CHEMBL448290

Cas Number: 574-25-4

PubChem CID: 676166

Product Number: M134692

Max Phase: Unknown

Molecular Formula: C10H12N4O4S

Molecular Weight: 284.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(S)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  NKGPJODWTZCHGF-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA448290

   THIOINOSINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 284.30

Molecular Weight (Monoisotopic): 284.0579

AlogP: -1.27

#Rotatable Bonds: 2

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.44

CX Basic pKa: ┄

CX LogP: -1.17

CX LogD: -1.44

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.40

Np Likeness Score: 0.98

References

1. Revankar GR, Hanna NB, Imamura N, Lewis AF, Larson SB, Finch RA, Avery TL, Robins RK..  (1990)  Synthesis and in vivo antitumor activity of 2-amino-9H-purine-6-sulfenamide, -sulfinamide, and -sulfonamide and related purine ribonucleosides.,  33  (1): [PMID:2296010] [10.1021/jm00163a020]

2. 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]

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. Iyengar BS, Dorr RT, Remers WA..  (1991)  Additional nucleotide derivatives of mitosenes. Synthesis and activity against parental and multidrug resistant L1210 leukemia.,  34  (7): [PMID:1906107] [10.1021/jm00111a004]

5. 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]

6. Srivastava PC, Revankar GR, Robins RK, Rousseau RJ..  (1981)  Synthesis and biological evaluation of certain 2'-deoxy-beta-D-ribo- and -beta-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine.,  24  (4): [PMID:7265126] [10.1021/jm00136a008]

7. Srivastava PC, Revankar GR, Robins RK, Rousseau RJ..  (1981)  Synthesis and biological evaluation of certain 2'-deoxy-beta-D-ribo- and -beta-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine.,  24  (4): [PMID:7265126] [10.1021/jm00136a008]

8. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

9. Li GX, Liu ZQ..  (2009)  Captopril and 6-mercaptopurine: whose SH possesses higher antioxidant ability?,  44  (12): [PMID:19692149] [10.1016/j.ejmech.2009.07.020]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

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. PubChem BioAssay data set, 

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

17. PubChem BioAssay data set, 

18. PubChem BioAssay data set, 

19. 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]

20. Pillaiyar T, Meenakshisundaram S, Manickam M, Sankaranarayanan M..  (2020)  A medicinal chemistry perspective of drug repositioning: Recent advances and challenges in drug discovery.,  195  [PMID:32283298] [10.1016/j.ejmech.2020.112275]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names