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-cyano-ethyl)-amide

ID: ALA609079

PubChem CID: 135976483

Max Phase: Preclinical

Molecular Formula: C15H18N6O6

Molecular Weight: 378.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H18N6O6/c16-2-1-3-18-12(25)6-4-21(11-8(6)13(26)20-15(17)19-11)14-10(24)9(23)7(5-22)27-14/h4,7,9-10,14,22-24H,1,3,5H2,(H,18,25)(H3,17,19,20,26)/t7-,9-,10-,14?/m1/s1

Standard InChI Key:  YXUXYEZGVKQCJA-FBFHGVSZSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.4750   -6.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -6.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -8.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -5.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -7.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -8.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1125   -1.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -9.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -6.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375   -4.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -9.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250   -7.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -8.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -3.4417    0.0000 C   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 17  3  0
 17 24  1  0
 18 15  2  0
  9 19  1  6
 20 12  1  0
 21  8  1  0
 22 15  1  0
 13 23  1  6
 24 27  1  0
 14 25  1  1
 26 25  1  0
 27 22  1  0
  4  2  1  0
 13 14  1  0
  8 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA609079

   ---

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: 378.35

Molecular Weight (Monoisotopic): 378.1288

AlogP: -2.03

#Rotatable Bonds: 5

Polar Surface Area: 199.77

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.02

CX Basic pKa: 1.97

CX LogP: -2.06

CX LogD: -2.06

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: 0.04

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