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

ID: ALA542697

PubChem CID: 45261573

Max Phase: Preclinical

Molecular Formula: C13H20ClN5O3S

Molecular Weight: 325.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Nc1[nH]cnc2c(C3NC(CSCCO)C(O)C3O)cnc1-2

Standard InChI:  InChI=1S/C13H19N5O3S.ClH/c14-13-10-8(16-5-17-13)6(3-15-10)9-12(21)11(20)7(18-9)4-22-2-1-19;/h3,5,7,9,11-12,18-21H,1-2,4,14H2,(H,16,17);1H

Standard InChI Key:  AQTUTBNKPUUFLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    7.3352   -3.2876    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
   -2.5735   -9.3109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301   -7.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174   -8.2010    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  2  0
  4  6  1  0
  4  7  1  0
  3  8  1  0
  2  9  1  0
  7  9  2  0
  8 10  1  0
  5 11  1  0
 10 11  1  0
  4 12  2  0
 12 13  1  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 22  1  0
 21 23  1  0
 22 23  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: 325.39

Molecular Weight (Monoisotopic): 325.1209

AlogP: -1.05

#Rotatable Bonds: 5

Polar Surface Area: 140.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.44

CX Basic pKa: 8.23

CX LogP: -2.87

CX LogD: -3.33

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: 0.41

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