(S)-1-[5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxysulfonylaminocarbonyl]-3-methylsulfanyl-propyl-ammonium

ID: ALA1163059

Chembl Id: CHEMBL1163059

PubChem CID: 447829

Max Phase: Preclinical

Molecular Formula: C15H23N7O7S2

Molecular Weight: 477.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@H](N)C(=O)NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H23N7O7S2/c1-30-3-2-7(16)14(25)21-31(26,27)28-4-8-10(23)11(24)15(29-8)22-6-20-9-12(17)18-5-19-13(9)22/h5-8,10-11,15,23-24H,2-4,16H2,1H3,(H,21,25)(H2,17,18,19)/t7-,8+,10+,11+,15+/m0/s1

Standard InChI Key:  PBPVXRRYIIRSNJ-JVEUSOJLSA-N

Alternative Forms

1. Parent:

   

   ALA1163059

   [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-[(2S)-2-amino-4-methylsulfanylbutanoyl]sulfamate

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: 477.53

Molecular Weight (Monoisotopic): 477.1100

AlogP: -2.51

#Rotatable Bonds: 9

Polar Surface Area: 217.80

Molecular Species: ACID

HBA: 14

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.74

CX Basic pKa: 6.78

CX LogP: -3.24

CX LogD: -3.26

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.25

Np Likeness Score: 0.52

References

1. Lee J, Kim SE, Lee JY, Kim SY, Kang SU, Seo SH, Chun MW, Kang T, Choi SY, Kim HO..  (2003)  N-Alkoxysulfamide, N-hydroxysulfamide, and sulfamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases.,  13  (6): [PMID:12643918] [10.1016/s0960-894x(03)00020-9]

2. Kim SE, Kim SY, Kim S, Kang T, Lee J..  (2005)  Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases.,  15  (14): [PMID:15951176] [10.1016/j.bmcl.2005.05.035]

3. Van de Vijver P, Vondenhoff GH, Denivelle S, Rozenski J, Verhaegen J, Van Aerschot A, Herdewijn P..  (2009)  Antibacterial 5'-O-(N-dipeptidyl)-sulfamoyladenosines.,  17  (1): [PMID:19070499] [10.1016/j.bmc.2008.11.054]

4. 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]

Source

Source(1):

• Scientific Literature