ID: ALA1163085

Max Phase: Preclinical

Molecular Formula: C19H23N7O8S

Molecular Weight: 509.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(=O)(=O)NC(=O)[C@@H](N)Cc2ccc(O)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H23N7O8S/c20-11(5-9-1-3-10(27)4-2-9)18(30)25-35(31,32)33-6-12-14(28)15(29)19(34-12)26-8-24-13-16(21)22-7-23-17(13)26/h1-4,7-8,11-12,14-15,19,27-29H,5-6,20H2,(H,25,30)(H2,21,22,23)/t11-,12+,14+,15+,19+/m0/s1

Standard InChI Key:  MJZAZMKENKZBAJ-QTOWJTHWSA-N

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

Properties

Molecular Weight: 509.50

Molecular Weight (Monoisotopic): 509.1329

AlogP: -2.32

#Rotatable Bonds: 8

Polar Surface Area: 238.03

Molecular Species: ACID

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.74

CX Basic pKa: 6.40

CX LogP: -2.54

CX LogD: -2.56

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: 0.73

References

1. Van de Vijver P, Ostrowski T, Sproat B, Goebels J, Rutgeerts O, Van Aerschot A, Waer M, Herdewijn P..  (2008)  Aminoacyl-tRNA synthetase inhibitors as potent and synergistic immunosuppressants.,  51  (10): [PMID:18438987] [10.1021/jm8000746]

2. Zhang B, De Graef S, Nautiyal M, Pang L, Gadakh B, Froeyen M, Van Mellaert L, Strelkov SV, Weeks SD, Van Aerschot A..  (2018)  Family-wide analysis of aminoacyl-sulfamoyl-3-deazaadenosine analogues as inhibitors of aminoacyl-tRNA synthetases.,  148  [PMID:29477072] [10.1016/j.ejmech.2018.02.013]

3. Nautiyal M, De Graef S, Pang L, Gadakh B, Strelkov SV, Weeks SD, Van Aerschot A..  (2019)  Comparative analysis of pyrimidine substituted aminoacyl-sulfamoyl nucleosides as potential inhibitors targeting class I aminoacyl-tRNA synthetases.,  173  [PMID:30995568] [10.1016/j.ejmech.2019.04.003]

Source

Source(1):

• Scientific Literature