2-amino-9-[2,3-dideoxy-3-(hydroxymethyl)-alpha-D-erythro-pentofuranosyl]-9H-purine-6(1H)-thione

ID: ALA3230222

PubChem CID: 23568330

Max Phase: Preclinical

Molecular Formula: C11H15N5O3S

Molecular Weight: 297.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ncn2[C@@H]2C[C@H](CO)[C@@H](CO)O2)c(=S)[nH]1

Standard InChI:  InChI=1S/C11H15N5O3S/c12-11-14-9-8(10(20)15-11)13-4-16(9)7-1-5(2-17)6(3-18)19-7/h4-7,17-18H,1-3H2,(H3,12,14,15,20)/t5-,6-,7+/m1/s1

Standard InChI Key:  JFXDHZJSWZPYOX-QYNIQEEDSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   11.2384  -10.5616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2384  -11.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9437  -11.7832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9437  -10.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6490  -10.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6490  -11.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4271  -11.6327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9081  -10.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4272  -10.3088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9437   -9.3317    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5313  -11.7884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6796  -12.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1999  -13.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6802  -13.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574  -12.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4276  -14.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1186  -13.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282  -14.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8651  -13.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  2  0
  2 11  1  0
 12  7  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  1  1
 15 18  1  6
 17 19  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3230222

   2-amino-9-[(2S,4R,5S)-4,5-bis(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione

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: 297.34

Molecular Weight (Monoisotopic): 297.0896

AlogP: -0.04

#Rotatable Bonds: 3

Polar Surface Area: 122.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: 1.44

CX LogP: -1.24

CX LogD: -1.24

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.59

Np Likeness Score: 0.68

References

1. Acton EM, Goerner RN, Uh HS, Ryan KJ, Henry DW, Cass CE, LePage GA..  (1979)  Improved antitumor effects in 3'-branched homologues of 2'-deoxythioguanosine. Synthesis and evaluation of thioguanine nucleosides of 2,3-dideoxy-3-(hydroxymethyl)-D-erythro-pentofuranose.,  22  (5): [PMID:582321] [10.1021/jm00191a012]

Source

Source(1):

• Scientific Literature