3-(beta-D-2-deoxyribofuranosyl)-10-methyl-1,3-diaza-2-oxophenoxazine

ID: ALA4873641

PubChem CID: 164620757

Max Phase: Preclinical

Molecular Formula: C16H17N3O5

Molecular Weight: 331.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1c2ccccc2Oc2cn([C@H]3C[C@H](O)[C@@H](CO)O3)c(=O)nc21

Standard InChI:  InChI=1S/C16H17N3O5/c1-18-9-4-2-3-5-11(9)23-12-7-19(16(22)17-15(12)18)14-6-10(21)13(8-20)24-14/h2-5,7,10,13-14,20-21H,6,8H2,1H3/t10-,13+,14+/m0/s1

Standard InChI Key:  URQLGQUGFZFHGV-ZLKJLUDKSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   21.4065  -10.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4054  -11.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8202  -10.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1116  -10.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8231  -11.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1122  -11.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1122  -12.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5340  -11.6585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5324  -12.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8209  -12.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8232  -13.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354  -14.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2469  -13.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2463  -12.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5365  -14.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8757  -15.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1294  -16.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9466  -16.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1979  -15.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6500  -16.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9834  -17.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9554  -14.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4279  -16.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2411  -11.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  1  0
  9 14  2  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 12  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 17 20  1  1
 20 21  1  0
 13 22  2  0
 18 23  1  6
  8 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873641

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.33

Molecular Weight (Monoisotopic): 331.1168

AlogP: 0.76

#Rotatable Bonds: 2

Polar Surface Area: 97.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: ┄

CX LogP: 0.04

CX LogD: 0.04

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 0.46

References

1. Kozlovskaya LI, Volok VP, Shtro AA, Nikolaeva YV, Chistov AA, Matyugina ES, Belyaev ES, Jegorov AV, Snoeck R, Korshun VA, Andrei G, Osolodkin DI, Ishmukhametov AA, Aralov AV..  (2021)  Phenoxazine nucleoside derivatives with a multiple activity against RNA and DNA viruses.,  220  [PMID:33894564] [10.1016/j.ejmech.2021.113467]

Source

Source(1):

• Scientific Literature