Deoxy-3',4'-didehydro-cytidine

ID: ALA5269958

Max Phase: Preclinical

Molecular Formula: C9H11N3O4

Molecular Weight: 225.20

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2OC(CO)=C[C@H]2O)c(=O)n1

Standard InChI:  InChI=1S/C9H11N3O4/c10-7-1-2-12(9(15)11-7)8-6(14)3-5(4-13)16-8/h1-3,6,8,13-14H,4H2,(H2,10,11,15)/t6-,8-/m1/s1

Standard InChI Key:  VQMYKNBUURJYAP-HTRCEHHLSA-N

Molfile:  

 
     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.9510   -0.1844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    0.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704    0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3471   -0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -0.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -1.3561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842    0.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    0.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1434   -0.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -1.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404   -0.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    0.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510    0.9863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704    1.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7734    1.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  6
  7  5  1  0
  3  8  1  0
  8  7  1  0
  7  9  1  1
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 16  9  1  0
 15 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269958

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 225.20

Molecular Weight (Monoisotopic): 225.0750

AlogP: -1.41

#Rotatable Bonds: 2

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.25

CX Basic pKa: ┄

CX LogP: -2.21

CX LogD: -2.21

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.57

Np Likeness Score: 1.15

References

1. Passow KT, Caldwell HS, Ngo KA, Arnold JJ, Antczak NM, Narayanan A, Jose J, Sturla SJ, Cameron CE, Ciota AT, Harki DA..  (2021)  A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide.,  64  (20.0): [PMID:34661397] [10.1021/acs.jmedchem.1c01481]

Source

Source(1):

• Scientific Literature