2',3'-didehydro-3'-deoxythymidine 5'-diphosphate

ID: ALA405730

PubChem CID: 461279

Max Phase: Preclinical

Molecular Formula: C10H14N2O10P2

Molecular Weight: 384.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H14N2O10P2/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(21-8)5-20-24(18,19)22-23(15,16)17/h2-4,7-8H,5H2,1H3,(H,18,19)(H,11,13,14)(H2,15,16,17)/t7-,8+/m0/s1

Standard InChI Key:  LXCAIISEDMYORY-JGVFFNPUSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -0.5278    2.2477    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    2.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    2.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    3.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    3.4852    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    3.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548    2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298    4.1997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    1.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.2997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -0.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259   -1.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -1.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -1.7518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -2.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0720   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2334   -3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -3.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388   -3.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -2.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100   -2.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045   -1.6655    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  1  0
  7  5  2  0
  8  5  1  0
 10  9  1  0
 11 10  1  1
 11 12  1  0
 13 11  1  0
 15 12  1  0
 14 13  2  0
 15 14  1  0
 15 16  1  1
 17 16  1  0
 24 16  1  0
 17 18  2  0
 17 19  1  0
 20 19  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA405730

   2',3'-Dehydro-2',3'-deoxy-thymidine 5'-diphosphate

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: 384.17

Molecular Weight (Monoisotopic): 384.0124

AlogP: -0.48

#Rotatable Bonds: 6

Polar Surface Area: 177.38

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: -0.78

CX LogD: -5.81

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: 1.08

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