AZTDP

ID: ALA265204

PubChem CID: 129170

Max Phase: Preclinical

Molecular Formula: C10H15N5O10P2

Molecular Weight: 427.20

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H15N5O10P2/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(24-8)4-23-27(21,22)25-26(18,19)20/h3,6-8H,2,4H2,1H3,(H,21,22)(H,12,16,17)(H2,18,19,20)/t6-,7+,8-/m0/s1

Standard InChI Key:  QOYVAFWJURKBJG-RNJXMRFFSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
   -2.0374   -7.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441   -7.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -8.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469   -8.9824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1666   -8.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8733   -8.9969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -7.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638   -7.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722   -6.5094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385   -9.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641  -10.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103  -11.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8361  -11.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983  -10.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3144  -11.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9690  -12.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474  -13.1683    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9257  -13.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1217  -12.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776  -13.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531  -14.4659    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9330  -15.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6768  -14.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338  -14.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229  -11.7306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483  -12.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784  -13.2438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  2  8  1  0
  8  9  2  0
 10  4  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 14  1  0
 13 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 12 25  1  6
 25 26  2  0
 26 27  2  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA265204

   1-{3-Azido-2,3-dideoxy-5-O-[hydroxy(phosphonooxy)phosphoryl]pentofuranosyl}-4-hydroxy-5-methylpyrimidin-2(1H)-one

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: 427.20

Molecular Weight (Monoisotopic): 427.0294

AlogP: 0.04

#Rotatable Bonds: 7

Polar Surface Area: 226.14

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: -0.84

CX LogD: -5.99

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: 1.10

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