(2R,3R,4S,5R)-2-(6-Amino-8-(dimethylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA3823299

PubChem CID: 6932036

Max Phase: Preclinical

Molecular Formula: C12H18N6O4

Molecular Weight: 310.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nc2c(N)ncnc2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H18N6O4/c1-17(2)12-16-6-9(13)14-4-15-10(6)18(12)11-8(21)7(20)5(3-19)22-11/h4-5,7-8,11,19-21H,3H2,1-2H3,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  ASFQZUKBYFITHP-IOSLPCCCSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.1003   -4.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501   -5.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7662   -4.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -5.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -6.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -3.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -3.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -2.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    2.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738    1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  3  9  1  0
  8 10  1  6
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 19  2  0
 10 19  1  0
 11 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3823299

   (2R,3R,4S,5R)-2-(6-Amino-8-(dimethylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 310.31

Molecular Weight (Monoisotopic): 310.1390

AlogP: -1.91

#Rotatable Bonds: 3

Polar Surface Area: 142.78

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.46

CX LogP: -1.30

CX LogD: -1.30

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: 0.65

References

1. Cheeseman MD, Westwood IM, Barbeau O, Rowlands M, Dobson S, Jones AM, Jeganathan F, Burke R, Kadi N, Workman P, Collins I, van Montfort RL, Jones K..  (2016)  Exploiting Protein Conformational Change to Optimize Adenosine-Derived Inhibitors of HSP70.,  59  (10): [PMID:27119979] [10.1021/acs.jmedchem.5b02001]

2. Li, Xiaokai and 8 more authors.  2013-11-14  Analogs of the Allosteric Heat Shock Protein 70 (Hsp70) Inhibitor, MKT-077, as Anti-Cancer Agents.  [PMID:24312699]

3. Cheeseman, Matthew D and 12 more authors.  2016-05-26  Exploiting Protein Conformational Change to Optimize Adenosine-Derived Inhibitors of HSP70.  [PMID:27119979]

4. Shao, Hao and 12 more authors.  2018-07-26  Exploration of Benzothiazole Rhodacyanines as Allosteric Inhibitors of Protein-Protein Interactions with Heat Shock Protein 70 (Hsp70).  [PMID:29953808]

Source

Source(1):

• Scientific Literature