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

ID: ALA2093901

Cas Number: 13153-62-3

PubChem CID: 40578255

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-ICQCTTRCSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    9.1008   -7.5021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1008   -8.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4328   -7.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7011   -6.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5232   -6.2233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -9.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7859   -7.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2215   -8.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6620   -9.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3195   -8.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1530   -5.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6278   -7.1767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3366   -5.7722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0797   -6.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2036   -9.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4157   -4.8188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -9.9572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3195   -7.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7827   -7.7419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2207   -4.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  1  0
 12  3  1  0
 13 14  1  0
 14 12  2  0
  6 15  1  1
 16 11  1  0
  9 17  1  6
 10 18  1  1
 19 18  1  0
 20 16  1  0
  5  4  1  0
  9 10  1  0
 11 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2093901

   (2R,3S,4S,5R)-2-(Hydroxymethyl)-5-(6-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

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. 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]

2. 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]

Source

Source(1):

• Scientific Literature