3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-one

ID: ALA4868090

PubChem CID: 11120681

Max Phase: Preclinical

Molecular Formula: C15H15N3O5

Molecular Weight: 317.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1nc2c(cn1[C@H]1C[C@H](O)[C@@H](CO)O1)Oc1ccccc1N2

Standard InChI:  InChI=1S/C15H15N3O5/c19-7-12-9(20)5-13(23-12)18-6-11-14(17-15(18)21)16-8-3-1-2-4-10(8)22-11/h1-4,6,9,12-13,19-20H,5,7H2,(H,16,17,21)/t9-,12+,13+/m0/s1

Standard InChI Key:  VNBPJJQDGPLSIV-ZWKOPEQDSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    8.2721   -9.2306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6964   -8.4055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2728   -8.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9842   -7.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9771   -7.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2591   -6.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5469   -7.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5577   -8.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6964   -9.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9823   -9.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9760  -10.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6819  -10.8695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3961  -10.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4041   -9.6421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1070  -10.8834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6769  -11.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0050  -12.1731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2528  -12.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0780  -12.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3400  -12.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7617  -13.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9419  -13.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5569  -13.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1 10  1  0
  9  2  1  0
  2  4  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  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
 13 15  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 16 12  1  1
 18 21  1  1
 21 22  1  0
 19 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4868090

   3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-10H-pyrimido[5,4-b][1,4]benzoxazin-2-one

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: 317.30

Molecular Weight (Monoisotopic): 317.1012

AlogP: 0.73

#Rotatable Bonds: 2

Polar Surface Area: 105.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: ┄

CX LogP: -0.13

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 0.67

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