{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid

ID: ALA259724

Cas Number: 491-97-4

PubChem CID: 164628

Max Phase: Preclinical

Molecular Formula: C10H16N2O11P2

Molecular Weight: 402.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H16N2O11P2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1

Standard InChI Key:  UJLXYODCHAELLY-XLPZGREQSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -0.8137    2.2100    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387    2.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113    2.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137    3.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5282    3.4475    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    3.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407    2.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1157    4.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137    1.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    0.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    0.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682   -0.3374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5513   -0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118   -1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132   -1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7982   -1.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626   -2.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -2.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -3.2106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -3.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187   -1.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  1  0
  1  4  1  0
  9  1  1  0
  4  5  1  0
  6  5  2  0
  7  5  1  0
  8  5  1  0
 10  9  1  0
 11 10  1  1
 11 12  1  0
 13 11  1  0
 16 12  1  0
 13 14  1  6
 15 13  1  0
 16 15  1  0
 16 17  1  1
 18 17  1  0
 25 17  1  0
 18 19  2  0
 18 20  1  0
 21 20  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA259724

   Thymidine-5'-diphosphate

Molecule Features

Natural Product: Yes

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: 402.19

Molecular Weight (Monoisotopic): 402.0229

AlogP: -1.28

#Rotatable Bonds: 6

Polar Surface Area: 197.61

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: -1.66

CX LogD: -6.70

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: 1.14

References

1. Hsu CH, Hu R, Dutschman GE, Yang G, Krishnan P, Tanaka H, Baba M, Cheng YC..  (2007)  Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.,  51  (5): [PMID:17353236] [10.1128/aac.01432-06]

Source

Source(1):

• Scientific Literature