2-amino-4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

ID: ALA216289

PubChem CID: 44416677

Max Phase: Preclinical

Molecular Formula: C21H24N4O7

Molecular Weight: 444.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(=O)C2=C(C1)OC(N)=C(C#N)C2c1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C21H24N4O7/c1-21(2)4-12(28)17-13(5-21)32-18(23)9(6-22)16(17)10-7-25(20(30)24-19(10)29)15-3-11(27)14(8-26)31-15/h7,11,14-16,26-27H,3-5,8,23H2,1-2H3,(H,24,29,30)/t11-,14+,15+,16?/m0/s1

Standard InChI Key:  PPSRFFUFXFSOAO-GHOLJIKESA-N

Molfile:  

     RDKit          2D

 32 35  0  0  1  0  0  0  0  0999 V2000
    2.1690   -5.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461   -4.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880   -4.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -7.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7402   -7.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7402   -7.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -8.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -7.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8845   -6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8845   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -9.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -9.9654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -8.3154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -7.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829   -8.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3362   -7.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9256   -6.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175   -7.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326   -7.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2561   -6.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1569   -7.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6432   -7.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -8.3154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -9.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -9.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8845   -9.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8845   -8.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -7.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326   -9.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -9.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1  2  1  0
  4  7  1  0
  8  5  1  0
  5  6  1  0
  6  7  2  0
  8  9  2  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11  1  1  0
  1 12  1  0
  4  9  1  0
 13 14  3  0
  7 13  1  0
  6 15  1  0
 10 16  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 19 22  1  6
 18 23  1  1
 23 24  1  0
 17 18  1  0
 21 25  1  1
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 26 31  2  0
 28 32  2  0
 29  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA216289

   2-amino-4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile

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: 444.44

Molecular Weight (Monoisotopic): 444.1645

AlogP: -0.37

#Rotatable Bonds: 3

Polar Surface Area: 180.66

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.59

CX Basic pKa: 1.93

CX LogP: -1.15

CX LogD: -1.15

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -0.09

References

1. Torrence PF, Fan X, Zhang X, Loiseau PM..  (2006)  Structurally diverse 5-substituted pyrimidine nucleosides as inhibitors of Leishmania donovani promastigotes in vitro.,  16  (19): [PMID:16879965] [10.1016/j.bmcl.2006.07.042]

2. Prichard MN, Keith KA, Johnson MP, Harden EA, McBrayer A, Luo M, Qiu S, Chattopadhyay D, Fan X, Torrence PF, Kern ER..  (2007)  Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.,  51  (5): [PMID:17325220] [10.1128/aac.01447-06]

Source

Source(1):

• Scientific Literature