(2R/S,3S/R)-4-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-[(methylsulfanyl)methyl]butane-1,2-diol trifluoroacetate salt

ID: ALA2070404

PubChem CID: 66553593

Max Phase: Preclinical

Molecular Formula: C15H22F3N5O4S

Molecular Weight: 311.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC[C@@H](CNCc1c[nH]c2c(N)ncnc12)[C@@H](O)CO.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C13H21N5O2S.C2HF3O2/c1-21-6-9(10(20)5-19)3-15-2-8-4-16-12-11(8)17-7-18-13(12)14;3-2(4,5)1(6)7/h4,7,9-10,15-16,19-20H,2-3,5-6H2,1H3,(H2,14,17,18);(H,6,7)/t9-,10+;/m1./s1

Standard InChI Key:  ZWCNRCGJCKEIQJ-UXQCFNEQSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    6.4478  -18.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394  -17.6253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4357  -18.8731    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294  -18.4539    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1672  -17.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8766  -18.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1772  -16.8195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311  -16.3100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703  -16.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0488  -15.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343  -14.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5569  -14.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8218  -14.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298  -15.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5450  -15.6762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2526  -15.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2405  -14.4318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5248  -14.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5131  -13.2081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1185  -15.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024  -16.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991  -17.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831  -17.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896  -15.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928  -15.0638    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800  -14.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1120  -17.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087  -18.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  5  6  1  0
  5  7  2  0
  8 20  1  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
 13 14  2  0
 22 23  1  6
 10 14  1  0
 21 24  1  1
 14 15  1  0
 24 25  1  0
 25 26  1  0
 15 16  2  0
 22 27  1  0
  8  9  1  0
 27 28  1  0
 16 17  1  0
 13 11  1  0
 17 18  2  0
 18 13  1  0
 11 12  1  0
 18 19  1  0
 12 10  2  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: 311.41

Molecular Weight (Monoisotopic): 311.1416

AlogP: -0.04

#Rotatable Bonds: 8

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: 13.39

CX Basic pKa: 8.84

CX LogP: -0.46

CX LogD: -1.91

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: 0.11

References

1. Clinch K, Evans GB, Fröhlich RF, Gulab SA, Gutierrez JA, Mason JM, Schramm VL, Tyler PC, Woolhouse AD..  (2012)  Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics.,  20  (17): [PMID:22854195] [10.1016/j.bmc.2012.07.006]

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