2-(4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-methylsulfanylmethyl-pyrrolidine-3,4-diol; 2hydrochloride

ID: ALA554322

PubChem CID: 45264876

Max Phase: Preclinical

Molecular Formula: C12H18ClN5O2S

Molecular Weight: 295.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC1NC(c2c[nH]c3c(N)ncnc23)C(O)C1O.Cl

Standard InChI:  InChI=1S/C12H17N5O2S.ClH/c1-20-3-6-10(18)11(19)8(17-6)5-2-14-9-7(5)15-4-16-12(9)13;/h2,4,6,8,10-11,14,17-19H,3H2,1H3,(H2,13,15,16);1H

Standard InChI Key:  DEDLSMPMUNDIQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    7.3352   -2.4930    0.0000 Cl  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
    2.1852   -2.6281    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
    1.2071   -3.7498    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
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5643   -3.1717    0.0000 C   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
    3.4539   -4.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -5.0249    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
   -2.3155    0.7475    0.0000 N   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
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805   -2.5334    0.0000 O   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
    4.3702   -5.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -6.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -6.6118    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158   -7.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
  2  6  1  0
  4  6  2  0
  4  7  1  0
  3  8  1  0
  2  9  2  0
  7  9  1  0
  8 10  1  0
  5 11  1  0
 10 11  1  0
  4 12  1  0
 12 13  2  0
  6 14  1  0
 13 15  1  0
 14 15  2  0
  8 16  1  0
 12 17  1  0
 10 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
M  END

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: 295.37

Molecular Weight (Monoisotopic): 295.1103

AlogP: -0.36

#Rotatable Bonds: 3

Polar Surface Area: 120.08

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.97

CX Basic pKa: 8.70

CX LogP: -0.66

CX LogD: -1.98

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 0.42

References

1. Evans GB, Furneaux RH, Schramm VL, Singh V, Tyler PC..  (2004)  Targeting the polyamine pathway with transition-state analogue inhibitors of 5'-methylthioadenosine phosphorylase.,  47  (12): [PMID:15163207] [10.1021/jm0306475]

2. Longshaw, Alistair I and 5 more authors.  2010-09-23  Design and synthesis of potent "sulfur-free" transition state analogue inhibitors of 5'-methylthioadenosine nucleosidase and 5'-methylthioadenosine phosphorylase.  [PMID:20718423]

3. Clinch, Keith and 8 more authors.  2012-09-01  Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics.  [PMID:22854195]

4. Evans, Gary B and 7 more authors.  2015-09-01  Tight binding enantiomers of pre-clinical drug candidates.  [PMID:26260335]

5. Harijan, Rajesh K and 7 more authors.  2019-04-11  Selective Inhibitors of Helicobacter pylori Methylthioadenosine Nucleosidase and Human Methylthioadenosine Phosphorylase.  [PMID:30860833]

Source

Source(1):

• Scientific Literature