9-alpha-D-Arabinofuranosyl-2-(methylthio)adenine

ID: ALA3248869

PubChem CID: 90673513

Max Phase: Preclinical

Molecular Formula: C11H15N5O4S

Molecular Weight: 313.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C11H15N5O4S/c1-21-11-14-8(12)5-9(15-11)16(3-13-5)10-7(19)6(18)4(2-17)20-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10+/m1/s1

Standard InChI Key:  AJNDEAZTAFKOOO-KMPDEGCQSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   13.2249  -13.7302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7447  -14.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9675  -14.1387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9675  -13.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3610  -12.7778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5277  -11.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3049  -11.7248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9114  -12.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7447  -13.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3042  -14.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3042  -15.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9675  -15.9162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5270  -15.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2765  -16.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0469  -15.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5270  -14.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2297  -15.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8574  -15.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6927  -12.0180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9197  -11.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0887  -10.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 10 16  1  0
 10  3  1  6
  8 19  1  0
  6 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3248869

   (2S,3S,4S,5R)-2-(6-amino-2-methylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-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: 313.34

Molecular Weight (Monoisotopic): 313.0845

AlogP: -1.26

#Rotatable Bonds: 3

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 5.17

CX LogP: -0.78

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.40

Np Likeness Score: 0.53

References

1. Montgomery JA, Shortnacy AT, Arnett G, Shannon WM..  (1977)  2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine and 9-alpha-D-arabinofuranosyl-8-azaadenine.,  20  (3): [PMID:191611] [10.1021/jm00213a017]

Source

Source(1):

• Scientific Literature