4-amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-(methylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

ID: ALA3823700

PubChem CID: 127050113

Max Phase: Preclinical

Molecular Formula: C13H16N6O4

Molecular Weight: 320.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1c(C#N)c2c(N)ncnc2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C13H16N6O4/c1-16-11-5(2-14)7-10(15)17-4-18-12(7)19(11)13-9(22)8(21)6(3-20)23-13/h4,6,8-9,13,16,20-22H,3H2,1H3,(H2,15,17,18)/t6-,8-,9-,13-/m1/s1

Standard InChI Key:  HHEUYEHDABDOIZ-HTVVRFAVSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    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 C   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
    6.1003   -4.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    3.7690    0.0000 N   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
  2  1  1  6
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  2  8  1  0
  7  9  1  6
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 12 18  2  0
  9 18  1  0
  1 19  1  0
 20 21  3  0
 11 20  1  0
 10 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3823700

   ---

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: 320.31

Molecular Weight (Monoisotopic): 320.1233

AlogP: -1.46

#Rotatable Bonds: 3

Polar Surface Area: 162.47

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.45

CX Basic pKa: 4.29

CX LogP: -1.86

CX LogD: -1.86

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: 0.40

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]

Source

Source(1):

• Scientific Literature