5'-deoxy-5'-N-(N-(2-hydroxybenzoyl)sulfamoyl)aminoadenosine

ID: ALA377483

Chembl Id: CHEMBL377483

Cas Number: 873556-29-7

PubChem CID: 11599426

Max Phase: Preclinical

Molecular Formula: C17H19N7O7S

Molecular Weight: 465.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CNS(=O)(=O)NC(=O)c2ccccc2O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H19N7O7S/c18-14-11-15(20-6-19-14)24(7-21-11)17-13(27)12(26)10(31-17)5-22-32(29,30)23-16(28)8-3-1-2-4-9(8)25/h1-4,6-7,10,12-13,17,22,25-27H,5H2,(H,23,28)(H2,18,19,20)/t10-,12-,13-,17-/m1/s1

Standard InChI Key:  CHPCUEVDLWQUFT-CNEMSGBDSA-N

Alternative Forms

1. Parent:

   

   ALA377483

   N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfamoyl]-2-hydroxybenzamide

2. Alternative Forms:

   

   ALA377483

   N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfamoyl]-2-hydroxybenzamide;N,N-diethylethanamine

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: 465.45

Molecular Weight (Monoisotopic): 465.1067

AlogP: -2.00

#Rotatable Bonds: 6

Polar Surface Area: 214.81

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.11

CX Basic pKa: 4.98

CX LogP: -1.63

CX LogD: -2.15

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: 0.21

References

1. Somu RV, Boshoff H, Qiao C, Bennett EM, Barry CE, Aldrich CC..  (2006)  Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis.,  49  (1): [PMID:16392788] [10.1021/jm051060o]

2. Qiao C, Gupte A, Boshoff HI, Wilson DJ, Bennett EM, Somu RV, Barry CE, Aldrich CC..  (2007)  5'-O-[(N-acyl)sulfamoyl]adenosines as antitubercular agents that inhibit MbtA: an adenylation enzyme required for siderophore biosynthesis of the mycobactins.,  50  (24): [PMID:17967002] [10.1021/jm070905o]

3. Soukarieh F, Williams P, Stocks MJ, Cámara M..  (2018)  Pseudomonas aeruginosa Quorum Sensing Systems as Drug Discovery Targets: Current Position and Future Perspectives.,  61  (23): [PMID:29999316] [10.1021/acs.jmedchem.8b00540]

Source

Source(1):

• Scientific Literature