2-Amino-7-((2R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (2-thiocarbamoyl-ethyl)-amide

ID: ALA607656

PubChem CID: 135976477

Max Phase: Preclinical

Molecular Formula: C15H20N6O6S

Molecular Weight: 412.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(S)CCNC(=O)c1cn(C2O[C@H](CO)[C@@H](O)[C@H]2O)c2nc(N)nc(O)c12

Standard InChI:  InChI=1S/C15H20N6O6S/c16-7(28)1-2-18-12(25)5-3-21(11-8(5)13(26)20-15(17)19-11)14-10(24)9(23)6(4-22)27-14/h3,6,9-10,14,22-24H,1-2,4H2,(H2,16,28)(H,18,25)(H3,17,19,20,26)/t6-,9-,10-,14?/m1/s1

Standard InChI Key:  LEWQIHKTBIUQJQ-JUTUJMCYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.9250   -6.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -5.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -8.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -5.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -6.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -7.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -8.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1125   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -9.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -6.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -4.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500   -1.9625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -9.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -8.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  0
  6  1  1  0
  7  3  2  0
  8  4  2  0
  9  5  1  0
 10 12  2  0
 11  5  1  0
 12  7  1  0
 13  9  1  0
 14 11  1  0
 15  2  1  0
 16 18  1  0
 17 16  2  0
 18 26  1  0
 19 15  2  0
 20 15  1  0
  9 21  1  6
 22 12  1  0
 23  8  1  0
 24 16  1  0
 13 25  1  6
 26 20  1  0
 14 27  1  1
 28 27  1  0
  4  2  1  0
 13 14  1  0
  8 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA607656

   ---

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: 412.43

Molecular Weight (Monoisotopic): 412.1165

AlogP: -1.64

#Rotatable Bonds: 6

Polar Surface Area: 199.83

Molecular Species: ZWITTERION

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.05

CX Basic pKa: 9.80

CX LogP: -1.95

CX LogD: -1.95

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: 0.29

References

1. Saito Y, Umezawa K, Kato K.  (1997)  Synthesis of echiguanine analogs and their ribofuranosyl glycosides that inhibit phosphatidylinositol 4-kinase,  7  (7): [10.1016/S0960-894X(97)00122-4]

Source

Source(1):

• Scientific Literature