N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-4-oxo-4H-benzo[e][1,2]oxazine-3-sulfonamide

ID: ALA4160378

Chembl Id: CHEMBL4160378

PubChem CID: 71819193

Max Phase: Preclinical

Molecular Formula: C18H17N7O7S

Molecular Weight: 475.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CNS(=O)(=O)c2noc3ccccc3c2=O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H17N7O7S/c19-15-11-16(21-6-20-15)25(7-22-11)18-14(28)13(27)10(31-18)5-23-33(29,30)17-12(26)8-3-1-2-4-9(8)32-24-17/h1-4,6-7,10,13-14,18,23,27-28H,5H2,(H2,19,20,21)/t10-,13-,14-,18-/m1/s1

Standard InChI Key:  RMWBJUAWZFLSAR-OXQGGJHDSA-N

Alternative Forms

1. Parent:

   

   ALA4160378

   N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-4-oxo-1,2-benzoxazine-3-sulfonamide

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: 475.44

Molecular Weight (Monoisotopic): 475.0910

AlogP: -1.49

#Rotatable Bonds: 5

Polar Surface Area: 208.58

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.37

CX Basic pKa: 3.94

CX LogP: -0.88

CX LogD: -1.60

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.08

References

1. Dawadi S, Boshoff HIM, Park SW, Schnappinger D, Aldrich CC..  (2018)  Conformationally Constrained Cinnolinone Nucleoside Analogues as Siderophore Biosynthesis Inhibitors for Tuberculosis.,  9  (4): [PMID:29670706] [10.1021/acsmedchemlett.8b00090]

Source

Source(1):

• Scientific Literature