N-((2S,3S,5R)-2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)anthracene-9-carboxamide

ID: ALA3578052

PubChem CID: 122178220

Max Phase: Preclinical

Molecular Formula: C25H23N3O5

Molecular Weight: 445.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](NC(=O)c3c4ccccc4cc4ccccc34)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C25H23N3O5/c1-14-12-28(25(32)27-23(14)30)21-11-19(20(13-29)33-21)26-24(31)22-17-8-4-2-6-15(17)10-16-7-3-5-9-18(16)22/h2-10,12,19-21,29H,11,13H2,1H3,(H,26,31)(H,27,30,32)/t19-,20+,21+/m0/s1

Standard InChI Key:  ABOGAJDPVPYUGH-PWRODBHTSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    6.6139    9.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4346    9.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    6.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    6.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    7.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3293    5.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930    7.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   10.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210    6.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824    8.7332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   10.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041    5.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378   11.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4573    8.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197   11.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4637   11.2814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    3.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120    3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    3.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 10  1  1
  8 11  2  0
  9 12  1  1
 14 10  1  0
 10  8  1  0
  6  9  1  0
 12  4  1  0
 13  2  1  0
  3  5  1  0
 13 15  2  0
  9  7  1  0
  2 14  2  0
  6  3  1  0
  8 16  1  0
 16 13  1  0
  2  1  1  0
  5  7  1  0
  6 17  1  6
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 19 25  2  0
 22 23  1  0
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 21 26  1  0
 21 22  2  0
 22 29  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 24 33  1  0
 24 25  1  0
 25 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3578052

   ---

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: 445.48

Molecular Weight (Monoisotopic): 445.1638

AlogP: 2.23

#Rotatable Bonds: 4

Polar Surface Area: 113.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.42

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: 0.14

References

1. Vernekar SK, Qiu L, Zhang J, Kankanala J, Li H, Geraghty RJ, Wang Z..  (2015)  5'-Silylated 3'-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus.,  58  (9): [PMID:25909386] [10.1021/acs.jmedchem.5b00327]

Source

Source(1):

• Scientific Literature