5'-O-(N-(2-hydroxybenzoyl)sulfamoyl)adenosine

ID: ALA371502

Chembl Id: CHEMBL371502

Cas Number: 863238-55-5

PubChem CID: 636430

Max Phase: Preclinical

Molecular Formula: C17H18N6O8S

Molecular Weight: 466.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: salicyl-AMS | Salicyl-AMS|863238-55-5|CHEMBL371502|5'-O-[(2-hydroxybenzoyl)sulfamoyl]adenosine|MMV687700|[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-hydroxybenzoyl)sulfamate|Salicyl-Adenosine Monosulfamate|SCHEMBL2288469|Salicyl-Adenosine Monosulphamate|salicylic adenosine monosulfamide|DTXSID301345783|BDBM50324670|AKOS040742786|5''-O-[N-(salicyl)sulfamoyl]adenosine|5'-O-[N-(salicyl)sulfamoyl]-adenosine|5''-O-[N-(salicyl)sulfamoyl] adenosine|MS-28592|5''-O-[N-(salicShow More⌵

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

Standard InChI:  InChI=1S/C17H18N6O8S/c18-14-11-15(20-6-19-14)23(7-21-11)17-13(26)12(25)10(31-17)5-30-32(28,29)22-16(27)8-3-1-2-4-9(8)24/h1-4,6-7,10,12-13,17,24-26H,5H2,(H,22,27)(H2,18,19,20)/t10-,12-,13-,17-/m1/s1

Standard InChI Key:  SABYITLYKSVAAD-CNEMSGBDSA-N

Alternative Forms

1. Parent:

   

   ALA371502

   Salicyl-AMS

2. Alternative Forms:

   

   ALA371502

   [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-hydroxybenzoyl)sulfamate;N,N-diethylethanamine
3. 

   ALA371502

   ---

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: 466.43

Molecular Weight (Monoisotopic): 466.0907

AlogP: -1.58

#Rotatable Bonds: 6

Polar Surface Area: 212.01

Molecular Species: ACID

HBA: 13

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.03

CX Basic pKa: 4.92

CX LogP: -1.61

CX LogD: -1.42

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: 0.46

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. Stirrett KL, Ferreras JA, Jayaprakash V, Sinha BN, Ren T, Quadri LE..  (2008)  Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis.,  18  (8): [PMID:18394884] [10.1016/j.bmcl.2008.03.025]

4. Gupte A, Boshoff HI, Wilson DJ, Neres J, Labello NP, Somu RV, Xing C, Barry CE, Aldrich CC..  (2008)  Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5'-O-[N-(salicyl)sulfamoyl]adenosine: antibacterial nucleosides effective against Mycobacterium tuberculosis.,  51  (23): [PMID:19053762] [10.1021/jm8008037]

5. Ferreras JA, Ryu JS, Di Lello F, Tan DS, Quadri LE..  (2005)  Small-molecule inhibition of siderophore biosynthesis in Mycobacterium tuberculosis and Yersinia pestis.,  1  (1): [PMID:16407990] [10.1038/nchembio706]

6. Moreau C, Kirchberger T, Swarbrick JM, Bartlett SJ, Fliegert R, Yorgan T, Bauche A, Harneit A, Guse AH, Potter BV..  (2013)  Structure-activity relationship of adenosine 5'-diphosphoribose at the transient receptor potential melastatin 2 (TRPM2) channel: rational design of antagonists.,  56  (24): [PMID:24304219] [10.1021/jm401497a]

7. Moreau C, Kirchberger T, Swarbrick JM, Bartlett SJ, Fliegert R, Yorgan T, Bauche A, Harneit A, Guse AH, Potter BV..  (2013)  Structure-activity relationship of adenosine 5'-diphosphoribose at the transient receptor potential melastatin 2 (TRPM2) channel: rational design of antagonists.,  56  (24): [PMID:24304219] [10.1021/jm401497a]

8. MMV Pathogen Box,  [10.6019/CHEMBL3637841]

9. Dawadi S, Kawamura S, Rubenstein A, Remmel R, Aldrich CC..  (2016)  Synthesis and pharmacological evaluation of nucleoside prodrugs designed to target siderophore biosynthesis in Mycobacterium tuberculosis.,  24  (6): [PMID:26875934] [10.1016/j.bmc.2016.02.002]

10. Nathan group, Weill Cornell Medical College; Barry Lab, NIAID NIH; Winzeler lab, UCSD; Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Univ. of Antwerp; London School of Hygiene and Tropical Medicine; Parasite Chemotherapy Unit at Swiss Tropical and Public Health Institute; Huston group at the University of Vermont; Castellanos group at UTMB, Galveston, Texas; Sakanari Lab, Univ. of Calif. San Francisco; Townson (Simon) Lab, Imperial College London; Fidelis Cho-Ngwa Lab, University of Buea, Buea, Cameroon; Laboratory of Molecular Parasitology at the New York Blood Center; Bickle Lab, London School of Hygiene and Tropical Medicine; Keiser Lab, Swiss Tropical and Public Health Institute; Caffrey group at the Center for Discovery and Innovation in Parasitic Diseases, Skaggs School of Pharmacy and Pharmaceutical Sciences, UC San Diego; University of Cape Town; Shanmugam group at CSIR-National Chemical Laboratory, Pune (India); Novartis Institute for Tropical Disease-Singapore; Abbvie. MMV Pathogen Box Bioactivity Data,  [10.6019/CHEMBL3832761]

11. Anna Ehmann. The Australian National University Dept Of Immunology Pathogen Box Compounds Screened,  [10.6019/CHEMBL3987221]

12. 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]

13. 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]

14. Sarink, M; Mykytyn, A; Tielens, A; van Hellemond, J. Naegleria gruberi Pathogen Box compounds screening,  [10.6019/CHEMBL4513101]

Source

Source(2):

• Scientific Literature
• MMV Pathogen Box