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[(S)-2-Amino-3-(1H-imidazol-4-yl)-propionyl]-sulfamic acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA412891

Chembl Id: CHEMBL412891

PubChem CID: 24752834

Max Phase: Preclinical

Molecular Formula: C16H21N9O7S

Molecular Weight: 483.47

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(=O)(=O)NC(=O)[C@@H](N)Cc2cnc[nH]2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H21N9O7S/c17-8(1-7-2-19-4-20-7)15(28)24-33(29,30)31-3-9-11(26)12(27)16(32-9)25-6-23-10-13(18)21-5-22-14(10)25/h2,4-6,8-9,11-12,16,26-27H,1,3,17H2,(H,19,20)(H,24,28)(H2,18,21,22)/t8-,9+,11+,12+,16+/m0/s1

Standard InChI Key:  WRXPXUSZYDNAQP-LEJQEAHTSA-N

Alternative Forms

Associated Targets(Human)

HARS1 Tchem Histidyl-tRNA synthetase (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PBMC (10003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 483.47Molecular Weight (Monoisotopic): 483.1285AlogP: -3.30#Rotatable Bonds: 8
Polar Surface Area: 246.48Molecular Species: ACIDHBA: 14HBD: 6
#RO5 Violations: 2HBA (Lipinski): 16HBD (Lipinski): 8#RO5 Violations (Lipinski): 2
CX Acidic pKa: 2.74CX Basic pKa: 6.90CX LogP: -5.06CX LogD: -4.75
Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.18Np Likeness Score: 0.54

References

1. Forrest AK, Jarvest RL, Mensah LM, O'Hanlon PJ, Pope AJ, Sheppard RJ..  (2000)  Aminoalkyl adenylate and aminoacyl sulfamate intermediate analogues differing greatly in affinity for their cognate Staphylococcus aureus aminoacyl tRNA synthetases.,  10  (16): [PMID:10969988] [10.1016/s0960-894x(00)00360-7]
2. 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