(Z)-1-(4-Amino-2-butenyl)cytosine

ID: ALA2261783

PubChem CID: 53232468

Max Phase: Preclinical

Molecular Formula: C8H12N4O

Molecular Weight: 180.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC/C=C\Cn1ccc(N)nc1=O

Standard InChI:  InChI=1S/C8H12N4O/c9-4-1-2-5-12-6-3-7(10)11-8(12)13/h1-3,6H,4-5,9H2,(H2,10,11,13)/b2-1-

Standard InChI Key:  IMZOZNSCWYZBQA-UPHRSURJSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   16.5439  -11.0286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1314  -11.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5439  -12.4576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3064  -11.7431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8939  -11.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0689  -11.0286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3064  -10.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1314  -10.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689  -11.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7814  -10.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689   -9.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5439   -9.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1314   -8.8852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  1  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  1  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2261783

   (Z)-1-(4-Amino-2-butenyl)cytosine

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: 180.21

Molecular Weight (Monoisotopic): 180.1011

AlogP: -0.66

#Rotatable Bonds: 3

Polar Surface Area: 86.93

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.65

CX LogP: -1.28

CX LogD: -3.47

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.60

Np Likeness Score: -0.21

References

1. Wittine K, Benci K, Kraljevic Pavelic S, Pavelic K, Bratulic S, Hock K, Balzarini J, Mintas M.  (2011)  Synthesis, cytostatic and anti-viral activity evaluation of the novel acyclic nucleoside analogues containing a sterically constrained (Z)-4-amino-2-butenyl moiety,  20  (3): [10.1007/s00044-010-9318-1]

Source

Source(1):

• Scientific Literature