2-[6-Amino-2-(N'-cyclohexylmethylene-hydrazino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA1950554

Max Phase: Phase

Molecular Formula: C17H25N7O4

Molecular Weight: 391.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Binodenoson | Wrc0470 | MRE-0470 | MRE0470

Trade Names(1): Corvue

Canonical SMILES:  Nc1nc(N/N=C/C2CCCCC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H25N7O4/c18-14-11-15(22-17(21-14)23-20-6-9-4-2-1-3-5-9)24(8-19-11)16-13(27)12(26)10(7-25)28-16/h6,8-10,12-13,16,25-27H,1-5,7H2,(H3,18,21,22,23)/b20-6+/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  XJFMHMFFBSOEPR-DNZQAUTHSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
   -0.7833   -0.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    0.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    0.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -0.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -0.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    1.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -3.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  6
  4  2  2  0
  5  2  1  0
  6  8  2  0
  7  3  1  0
  8  1  1  0
  9 12  1  0
 10  3  1  0
 11  4  1  0
 12  5  2  0
 13  7  1  0
 14 10  1  0
 15 16  1  0
 16 12  1  0
  7 17  1  1
 18 11  1  0
 13 19  1  1
 20 15  2  0
 14 21  1  6
 22 21  1  0
 23 20  1  0
 24 23  1  0
 25 23  1  0
 26 25  1  0
 27 24  1  0
 28 26  1  0
  6  4  1  0
 14 13  1  0
 11  9  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950554

   BINODENOSON

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.43

Molecular Weight (Monoisotopic): 391.1968

AlogP: 0.00

#Rotatable Bonds: 5

Polar Surface Area: 163.93

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.81

CX Basic pKa: 4.77

CX LogP: 0.46

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: 0.42

References

1. Niiya K, Olsson RA, Thompson RD, Silvia SK, Ueeda M..  (1992)  2-(N'-alkylidenehydrazino)adenosines: potent and selective coronary vasodilators.,  35  (24): [PMID:1469687] [10.1021/jm00102a007]

2. Deflorian F, Kumar TS, Phan K, Gao ZG, Xu F, Wu H, Katritch V, Stevens RC, Jacobson KA..  (2012)  Evaluation of molecular modeling of agonist binding in light of the crystallographic structure of an agonist-bound A₂A adenosine receptor.,  55  (1): [PMID:22104008] [10.1021/jm201461q]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. El-Tayeb A, Gollos S..  (2013)  Synthesis and structure-activity relationships of 2-hydrazinyladenosine derivatives as A(2A) adenosine receptor ligands.,  21  (2): [PMID:23245803] [10.1016/j.bmc.2012.11.021]

5. de Lera Ruiz M, Lim YH, Zheng J..  (2014)  Adenosine A2A receptor as a drug discovery target.,  57  (9): [PMID:24164628] [10.1021/jm4011669]

6. Preti D, Baraldi PG, Saponaro G, Romagnoli R, Aghazadeh Tabrizi M, Baraldi S, Cosconati S, Bruno A, Novellino E, Vincenzi F, Ravani A, Borea PA, Varani K..  (2015)  Design, synthesis, and biological evaluation of novel 2-((2-(4-(substituted)phenylpiperazin-1-yl)ethyl)amino)-5'-N-ethylcarboxamidoadenosines as potent and selective agonists of the A2A adenosine receptor.,  58  (7): [PMID:25780876] [10.1021/acs.jmedchem.5b00215]

7. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names