2-Amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-methanesulfonyl-1,9-dihydro-purin-6-one

ID: ALA606271

PubChem CID: 135976322

Max Phase: Preclinical

Molecular Formula: C11H15N5O7S

Molecular Weight: 361.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1nc2c(O)nc(N)nc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H15N5O7S/c1-24(21,22)11-13-4-7(14-10(12)15-8(4)20)16(11)9-6(19)5(18)3(2-17)23-9/h3,5-6,9,17-19H,2H2,1H3,(H3,12,14,15,20)/t3-,5-,6-,9?/m1/s1

Standard InChI Key:  AVRXZAZVHJOTBC-LZGMGDPASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.9667   -0.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375    0.5208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -0.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    1.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500    1.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -2.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -2.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  2  0
  6  3  1  0
  7  2  1  0
  8  3  2  0
  9  4  1  0
 10 13  2  0
 11  4  1  0
 12  6  2  0
 13  8  1  0
 14  9  1  0
 15 11  1  0
 16  7  2  0
 17  7  2  0
  9 18  1  6
 19 13  1  0
 20 12  1  0
 14 21  1  6
 22  7  1  0
 15 23  1  1
 24 23  1  0
  5  6  1  0
 15 14  1  0
 12 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA606271

   ---

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: 361.34

Molecular Weight (Monoisotopic): 361.0692

AlogP: -2.87

#Rotatable Bonds: 3

Polar Surface Area: 193.91

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.25

CX Basic pKa: ┄

CX LogP: -2.19

CX LogD: -2.19

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: 0.34

References

1. Lin TS, Cheng JC, Ishiguro K, Sartorelli AC..  (1985)  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.,  28  (9): [PMID:3861870] [10.1021/jm00147a012]

Source

Source(1):

• Scientific Literature