ID: ALA236537

Max Phase: Preclinical

Molecular Formula: C10H13N5O5

Molecular Weight: 283.24

Molecule Type: Small molecule

Representations

Synonyms (1): N6-Hydroxyadenosine
Synonyms from Alternative Forms(1):

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3/c(=N\O)[nH]cnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H13N5O5/c16-1-4-6(17)7(18)10(20-4)15-3-13-5-8(14-19)11-2-12-9(5)15/h2-4,6-7,10,16-19H,1H2,(H,11,12,14)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  QROZCFCNYCVEDO-KQYNXXCUSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 283.24

Molecular Weight (Monoisotopic): 283.0917

AlogP: -2.34

#Rotatable Bonds: 2

Polar Surface Area: 149.01

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.52

CX Basic pKa: 1.88

CX LogP: -2.36

CX LogD: -3.07

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.31

Np Likeness Score: 1.40

References

1. Shealy YF, O'Dell CA, Shannon WM, Arnett G..  (1984)  Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.,  27  (11): [PMID:6092635] [10.1021/jm00377a007]

2. Kusachi S, Thompson RD, Bugni WJ, Yamada N, Olsson RA..  (1985)  Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.,  28  (11): [PMID:2999397] [10.1021/jm00149a016]

3. Cristalli G, Vittori S, Eleuteri A, Grifantini M, Volpini R, Lupidi G, Capolongo L, Pesenti E..  (1991)  Purine and 1-deazapurine ribonucleosides and deoxyribonucleosides: synthesis and biological activity.,  34  (7): [PMID:2066996] [10.1021/jm00111a044]

4. Too K, Brown DM, Bongard E, Yardley V, Vivas L, Loakes D..  (2007)  Anti-malarial activity of N6-modified purine analogues.,  15  (16): [PMID:17548196] [10.1016/j.bmc.2007.05.038]

5. Graci JD, Too K, Smidansky ED, Edathil JP, Barr EW, Harki DA, Galarraga JE, Bollinger JM, Peterson BR, Loakes D, Brown DM, Cameron CE..  (2008)  Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.,  52  (3): [PMID:18180344] [10.1128/aac.01056-07]

6. Cappellacci L, Petrelli R, Franchetti P, Vita P, Kusumanchi P, Kumar M, Jayaram HN, Zhou B, Yen Y, Grifantini M..  (2011)  Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.,  46  (5): [PMID:21349610] [10.1016/j.ejmech.2011.01.055]

7. PubChem BioAssay data set, 

8. Dymińska L..  (2015)  Imidazopyridines as a source of biological activity and their pharmacological potentials-Infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials.,  23  (18): [PMID:26314922] [10.1016/j.bmc.2015.07.045]

9. Indorf P, Kubitza C, Scheidig AJ, Kunze T, Clement B..  (2020)  Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.,  63  (12): [PMID:31790578] [10.1021/acs.jmedchem.9b01483]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays