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

ID: ALA150348

PubChem CID: 44366748

Max Phase: Preclinical

Molecular Formula: C16H22N6O5S

Molecular Weight: 410.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/N=C(\S)OC[C@H]1OC(n2cnc3c(NC4CCOC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H22N6O5S/c1-17-16(28)26-5-9-11(23)12(24)15(27-9)22-7-20-10-13(18-6-19-14(10)22)21-8-2-3-25-4-8/h6-9,11-12,15,23-24H,2-5H2,1H3,(H,17,28)(H,18,19,21)/t8?,9-,11-,12-,15?/m1/s1

Standard InChI Key:  OXVAPEGCPANDNE-ATJVVDHWSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
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   -0.0583   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500   -1.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -3.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -3.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625   -1.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -4.1667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083   -2.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875   -3.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708   -3.7542    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  1  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  4  2  0
 10  6  1  0
 11  8  1  0
 12  3  2  0
 13 16  2  0
 14 19  1  0
 15  9  1  0
 16 12  1  0
 17 14  1  0
 11 18  1  1
 19 18  1  0
  6 20  1  6
 21 14  2  0
 22 27  1  0
 10 23  1  6
 15 24  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
 13  9  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA150348

   Methyl-thiocarbamic acid (2R,3S,4R)-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: 410.46

Molecular Weight (Monoisotopic): 410.1372

AlogP: -0.42

#Rotatable Bonds: 5

Polar Surface Area: 136.14

Molecular Species: ZWITTERION

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.45

CX Basic pKa: 8.79

CX LogP: -0.26

CX LogD: -1.04

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: 0.65

References

1. 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