Methyl-carbamic acid (2R,3R,5R)-3,4-dihydroxy-5-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester

ID: ALA150950

PubChem CID: 44366934

Max Phase: Preclinical

Molecular Formula: C16H22N6O6

Molecular Weight: 394.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)OC[C@H]1OC(n2cnc3c(NC4CCOC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H22N6O6/c1-17-16(25)27-5-9-11(23)12(24)15(28-9)22-7-20-10-13(18-6-19-14(10)22)21-8-2-3-26-4-8/h6-9,11-12,15,23-24H,2-5H2,1H3,(H,17,25)(H,18,19,21)/t8?,9-,11-,12-,15?/m1/s1

Standard InChI Key:  PAXXXZVJWGPTHT-ATJVVDHWSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.7792   -0.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -0.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042    0.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    1.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    0.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -2.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -0.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3167    2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -2.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167    2.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    2.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125    3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  4  1  0
 10  6  1  0
 11  8  1  0
 12  3  1  0
 13 16  1  0
 14 18  1  0
 15  9  1  0
 16 12  2  0
 11 17  1  1
 18 17  1  0
 19 14  2  0
  6 20  1  6
 21 14  1  0
 22 27  1  0
 10 23  1  6
 24 15  1  0
 25 24  1  0
 26 25  1  0
 27 24  1  0
 28 21  1  0
  5  4  1  0
 10 11  1  0
  9 13  2  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA150950

   Methyl-carbamic acid (2R,3R,5R)-3,4-dihydroxy-5-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester

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: 394.39

Molecular Weight (Monoisotopic): 394.1601

AlogP: -1.00

#Rotatable Bonds: 5

Polar Surface Area: 152.88

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.45

CX Basic pKa: 4.68

CX LogP: -1.56

CX LogD: -1.56

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: 0.66

References

1. Morrison CF, Elzein E, Jiang B, Ibrahim PN, Marquart T, Palle V, Shenk KD, Varkhedkar V, Maa T, Wu L, Wu Y, Zeng D, Fong I, Lustig D, Leung K, Zablocki JA..  (2004)  Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.,  14  (14): [PMID:15203164] [10.1016/j.bmcl.2004.04.096]

2. Palle VP, Varkhedkar V, Ibrahim P, Ahmed H, Li Z, Gao Z, Ozeck M, Wu Y, Zeng D, Wu L, Leung K, Chu N, Zablocki JA..  (2004)  Affinity and intrinsic efficacy (IE) of 5'-carbamoyl adenosine analogues for the A1 adenosine receptor--efforts towards the discovery of a chronic ventricular rate control agent for the treatment of atrial fibrillation (AF).,  14  (2): [PMID:14698198] [10.1016/j.bmcl.2003.09.094]

Source

Source(1):

• Scientific Literature