2-(6-Hydrazino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA236757

Chembl Id: CHEMBL236757

Cas Number: 5746-27-0

PubChem CID: 7075199

Max Phase: Preclinical

Molecular Formula: C10H14N6O4

Molecular Weight: 282.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N6-Aminoadenosine | N6-aminoadenosine|CHEMBL236757|5746-27-0|1-Aminoadenosine|N-aminoadenosine|Inosine, hydrazone|SCHEMBL8712645|BDBM50214817|NSC 29408|AKOS030488442|9H-Purine, 6-hydrazino-9-beta-D-ribofuranosyl-|(2R,3R,4S,5R)-2-(6-hydrazinyl-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Canonical SMILES:  NNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H14N6O4/c11-15-8-5-9(13-2-12-8)16(3-14-5)10-7(19)6(18)4(1-17)20-10/h2-4,6-7,10,17-19H,1,11H2,(H,12,13,15)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  DGKZTAGCCXJUAT-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA236757

   N6-aminoadenosine

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

Calculated Properties

Molecular Weight: 282.26

Molecular Weight (Monoisotopic): 282.1077

AlogP: -2.28

#Rotatable Bonds: 3

Polar Surface Area: 151.57

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.45

CX Basic pKa: 9.00

CX LogP: -1.87

CX LogD: -2.55

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.31

Np Likeness Score: 0.80

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. 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. Ha SB, Melman N, Jacobson KA, Nair V.  (1997)  New base-altered adenosine analogues: Synthesis and affinity at adenosine A1 and A2A receptors,  7  (24): [10.1016/S0960-894X(97)10177-9]

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. Tosh DK,Brackett CM,Jung YH,Gao ZG,Banerjee M,Blagg BSJ,Jacobson KA.  (2021)  Biological Evaluation of 5'-(N-Ethylcarboxamido)adenosine Analogues as Grp94-Selective Inhibitors.,  12  (3): [PMID:33738064] [10.1021/acsmedchemlett.0c00509]

Source

Source(1):

• Scientific Literature