Sulfamic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA471144

Chembl Id: CHEMBL471144

PubChem CID: 97576

Max Phase: Preclinical

Molecular Formula: C10H14N6O6S

Molecular Weight: 346.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5'-O-(Sulfamoyl)Adenosine | 5'-O-Sulfamoyladenosine | 5'-O-sulfamoyladenosine|CHEMBL471144|[(2R,3S,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDRO-2-FURANYL]METHYL SULFAMATE|LMS|Adenosine, 5'-sulfamate|EA 68|5'-o-sulfamoyl adenosine|5'-O-(sulfamoyl)adenosine|5''''-O-Sulfamoyladenosine|SCHEMBL2294870|9H-Purin-6-amine, 9-[5-O-(aminosulfonyl)-.beta.-D-ribofuranosyl]-|5''''-O-(Sulfamoyl)Adenosine|BDBM50454088|NSC804678|DB02916|NSC 133114|NSC-804678|PD059758|NS00070555|[(2R,3S,4R,5R)-5-(6-amShow More⌵

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

Standard InChI:  InChI=1S/C10H14N6O6S/c11-8-5-9(14-2-13-8)16(3-15-5)10-7(18)6(17)4(22-10)1-21-23(12,19)20/h2-4,6-7,10,17-18H,1H2,(H2,11,13,14)(H2,12,19,20)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  GNZLUJQJDPRUTD-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA471144

   [(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-YL)-3,4-dihydroxytetrahydro-2-furanyl]methyl 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: 346.33

Molecular Weight (Monoisotopic): 346.0696

AlogP: -2.75

#Rotatable Bonds: 4

Polar Surface Area: 188.70

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.30

CX Basic pKa: 3.94

CX LogP: -2.61

CX LogD: -2.61

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: 0.81

References

1. Siddiqi SM, Jacobson KA, Esker JL, Olah ME, Ji XD, Melman N, Tiwari KN, Secrist JA, Schneller SW, Cristalli G..  (1995)  Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.,  38  (7): [PMID:7707320] [10.1021/jm00007a014]

2. Neres J, Labello NP, Somu RV, Boshoff HI, Wilson DJ, Vannada J, Chen L, Barry CE, Bennett EM, Aldrich CC..  (2008)  Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: structure-activity relationships of the nucleobase domain of 5'-O-[N-(salicyl)sulfamoyl]adenosine.,  51  (17): [PMID:18690677] [10.1021/jm800567v]

3. 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]

4. Lukkarila JL, da Silva SR, Ali M, Shahani VM, Xu GW, Berman J, Roughton A, Dhe-Paganon S, Schimmer AD, Gunning PT..  (2011)  Identification of NAE Inhibitors Exhibiting Potent Activity in Leukemia Cells: Exploring the Structural Determinants of NAE Specificity.,  2  (8): [PMID:24900352] [10.1021/ml2000615]

5. Gough GR, Nobbs DM, Middleton JC, Penglis-Caredes F, Maguire MH..  (1978)  New inhibitors of platelet aggregation. 5'-Phosphate, 5'-phosphorothioate, and 5'-O-sulfamoyl derivatives of 2-substituted adenosine analogues.,  21  (6): [PMID:671448] [10.1021/jm00204a004]

6. Mujumdar P, Bua S, Supuran CT, Peat TS, Poulsen SA..  (2018)  Synthesis, structure and bioactivity of primary sulfamate-containing natural products.,  28  (17): [PMID:29685656] [10.1016/j.bmcl.2018.04.038]

Source

Source(1):

• Scientific Literature