4'-ethynylD4TDP

ID: ALA265460

PubChem CID: 44452717

Max Phase: Preclinical

Molecular Formula: C12H14N2O10P2

Molecular Weight: 408.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4'-ethynylD4TDP | 4'-ethynylD4TDP|CHEMBL265460

Canonical SMILES:  C#CC1=C[C@H](n2cc(C)c(=O)[nH]c2=O)O[C@@H]1COP(=O)(O)OP(=O)(O)O

Standard InChI:  InChI=1S/C12H14N2O10P2/c1-3-8-4-10(14-5-7(2)11(15)13-12(14)16)23-9(8)6-22-26(20,21)24-25(17,18)19/h1,4-5,9-10H,6H2,2H3,(H,20,21)(H,13,15,16)(H2,17,18,19)/t9-,10-/m1/s1

Standard InChI Key:  ZQSBZSGVKLGHPO-NXEZZACHSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  1  0  0  0  0  0999 V2000
    4.3380  -12.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238  -13.2883    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363  -14.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097  -13.7008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2113  -12.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863  -12.5742    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863  -13.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613  -12.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863  -11.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005  -11.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005  -10.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326  -10.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -9.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5130   -9.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683  -10.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0004   -8.5759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -7.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1484   -7.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -6.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052   -7.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178   -8.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525   -9.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -6.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484  -10.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625  -10.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 11 15  1  0
 14 16  1  6
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 16 22  1  0
 22 23  2  0
 18 24  1  0
 12 25  1  0
  1  2  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA265460

   4'-ethynylD4TDP

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: 408.20

Molecular Weight (Monoisotopic): 408.0124

AlogP: -0.47

#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: -0.90

CX LogD: -5.93

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: 0.68

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